


Gabriel's Ill-Advised Ways to Win Your Man

by JinxedAmbitions



Category: Supernatural
Genre: Alternate Universe, Awkward Castiel, Comedy, Engaged Dean/Lisa, F/M, Kind of Stripper Castiel, M/M, Panic Attack, Romance, Stripping
Language: English
Status: Completed
Published: 2014-01-17
Updated: 2015-07-05
Packaged: 2018-01-09 00:05:14
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 24,311
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1139085
Author URL: https://archiveofourown.org/users/JinxedAmbitions/pseuds/JinxedAmbitions
Summary: <blockquote class="userstuff">
              <p>Castiel was in love with Dean Winchester from the moment Cas drunkenly stumbled into him in his dorm.  Now nearly ten years later, Dean is successful and getting married while Castiel is reminded that he has neither the man nor the career he wanted.  But that's all going to change if Gabriel has anything to say about it.  He has the perfect plan to help Cas snag Dean before the big wedding.  He just needs to teach Cas to take his clothes off and dance like a pro before Dean's bachelor party.</p>
            </blockquote>





	1. An Upsetting Development

Castiel sat at his cluttered desk with his face propped against his left hand while he perused the article he was supposed to be editing for publication. Cas' stormy blue eyes were fighting not to close from lack of sleep and boredom with the latest findings in the mating habits of chimpanzees. There was a brief knock on the door to his office before it was thrown open. Gabriel, his closest friend in the office and out of it, walked in without apology holding a folded up newspaper. Castiel watched as the short man walked up to his desk and dropped the paper on top of the article Cas hadn't been reading.

“Page fourteen, second column, halfway down the page,” Gabe said putting his hands on his hips and taking the stance of someone who was slightly too impatient for propriety. Castiel carded his fingers through his dark brown hair as he unfolded the paper with his other hand. He rolled her eyes when Gabriel's foot began to tap repeatedly.  

“Personal ads, really Gabriel? Is that something you interrupt my work for these days?” Castiel asked when he found the page. However, his words stopped when he found the ad that Gabe had wanted him to see. “Oh, that's a mood killer, now, isn't it,” he said as he let the paper slip through his finger and back onto the already overburdened desk. Circled in pink highlighter, just in case the name and picture hadn't been enough of a tip off to Castiel, was a wedding announcement for one, Dean Winchester.

“Cassie, that's a life ruiner. Did you read what he does for a living? He's probably loaded, and here you are editing articles about chimpanzee sex,” Gabriel said in a blunt way that was irritating yet endearing, because his filter had been lost in a rain storm long ago and washed down into the sewer. Castiel looked up into his friend's pitying gold eyes and back at the ad.  He could hear Gabriel unwrapping some sort of candy while he read.

 _Congratulations to our daughter, Lisa Braeden, and Dean Winchester on their impending nuptials. Lisa, senior event planner at Lasting Memories, and Dean, partner at Meadows, Larkin, and Larkin, will be married on June 16_ _th_ _at the St. John's church._

Castiel stopped reading after that. Meadows, Larkin, and Larkin was the biggest firm in the city, possibly the state, and Castiel didn't even want to think about whose balls one had to gargle in order to make partner there. He neatly folded up the paper again, and held it up for Gabriel to take back to his station outside the VP's office. Castiel could feel the pity dripping off of his stout, obnoxious friend, but he refused to look him in the eye.

“I told you that you should have slept with him that time he was wasted and willing to screw anything with a pulse at that frat party sophomore year,” Gabriel said in a conversational tone as he accepted the paper back.

“I believe they call that rape in most circles, Gabriel,” Castiel said as he leaned back in his chair and gazed out the window overlooking the expansive city. He'd nearly had to cripple three other employees to secure an office with a window when it had opened up. He was truly sad that Ernie had had a nervous breakdown, really he was, but window offices didn't open up very often. He'd simply done what three other employees were not prepared to do. That was reorganize the vice presidents file room, which had taken three whole weeks, so Castiel felt justified in being the youngest employee with such a perk. It also meant he had his own office as opposed to a cubicle, so he could close the blinds and sleep if articles on primate biology became too overwhelmingly boring for him.

Castiel had a PhD in biology as well as a second Bachelor's degree in chemistry. He was even well published for a man who had yet to turn thirty, but instead of finding a career in a lab or at a prestigious university, he chose to sit at a desk and read other people's often poorly written work for a living. Working for a popular science magazine meant Castiel was in charge of making the magazine publishable, not Dr. Rufus Turner, former tenured and distinguished professor of biology and chief editor, because to be honest, Dr. Turner didn't care much about other scientists' findings, and semicolons still baffled him. Instead, Castiel was underpaid and overburdened with endless articles to edit and accept or decline while staring out across the small city.

Gabriel gave him one last pitying glance before retreating back to his desk in front of the offices on the top floor. No doubt Zachariah Adler, the VP, would be back from his lunch meeting soon. Castiel sighed and leaned back in his overstuffed and far-too-comfy-to-promote-productivity office chair. Dean Winchester was getting married and it wasn't to him, and he probably didn't remember who Castiel was if he had even known in the first place.

Castiel, Gabriel, and Dean had all attended the same college in undergrad. Dean had been two years ahead of Cas and Gabe, and he'd been a resident assistant in Gabriel's building. Castiel had literally run into him while Cas was drunk and Dean was in just a towel. It would have been embarrassing had Cas had the capacity for shame at that moment, but instead he'd laughed uncontrollably as he sat on his ass staring up at Dean. He had been remarkably cool about the whole situation, his state of undress, Cas' obvious underage drinking, the fact that it was three in the morning and Cas was not in his own building. Dean had helped him up and made sure he arrived at Gabe's dorm room without further incident.

Castiel had been mildly in love with Dean ever since he'd fallen into Gabriel's arms giggling that night. Dean had only been Gabe's RA for one more semester before Dean moved in with friends, but the boys had a tendency to see him at parties they went to from time to time. They never spoke unless one or both parties were particularly drunk, but Castiel had seemed content to live just knowing the man of his dreams existed. Gabriel rolled his eyes at his awkward counterpart regularly. Castiel was tall and athletically built. Apart from his habit to stare openly and lack of understanding when it came to personal space, Castiel was a catch. Yet, Cas had been too shy to approach most of the men he had taken an interest in throughout their college years, Dean being no exception.

There had been that one time where Dean had been particularly drunk after what Castiel and Gabriel had assumed was a pretty nasty break up. He'd insisted on dancing with the pair of them, and had propositioned Castiel, going so far as to say Gabriel could join if it would make him more comfortable. Castiel had looked to Gabriel like a deer in headlights, and Gabe had encouraged him to jump on that like it was going out of fashion. Instead, Castiel had forced Gabriel to help him drag Dean back to his house. Gabriel had had to climb in the kitchen window, because Dean seemed to have lost his keys as some point in the night. They'd put him to bed on his side, and Castiel had left a pair of aspirin and two bottles of water on his night table. At least, he had hoped it was Dean's nightstand and not another roommate's.

They hadn't seen him at any parties after that night. They assumed he had no idea who'd taken him home, and Castiel had seemed to be okay with that even if Gabriel knew he was disappointed that Dean had been far too drunk to hook up. Dean had graduated the following spring and gone away to law school, so he just became a guy that they joked about. Until, his wedding announcement darkened the pages of the local paper.

***

“Who even cares if Dean Winchester is getting married?” Cas asked his cat, Balthazar. The gray tabby was curled in his lap while he sat on the fire escape of his apartment. A bottle of red wine was sitting next to him, half empty. He'd opted out of using a glass since he'd forgotten to do his dishes for the last few days. “He wouldn't want me even if he didn't have a wonderful, successful fiancee,” he mumbled as he ran his finger's through Balthazar's soft fur. “I have a PhD that's collecting dust beside all the bills I can barely pay. Gabriel says I'm still awkward and creepy sometimes. The only dishes I've washed in the past week are your food and water bowls, and I talk to my cat. I'm not exactly epic romance material.”

Balthazar's only reply was a rumbling purr that grew louder when Cas rubbed beneath his jaw. Castiel sighed dejectedly and took another swig out of the bottle of wine.

“Cassie, you home?” Gabriel called from within the apartment. Cas considered remaining quiet in hopes that his friend would go away, but Gabriel was never so easily dissuaded.

“On the fire escape,” Castiel called through the open window. He could hear Gabriel moving around in the apartment for a couple minutes before his head popped out the window. He was wearing the expression Cas had come to refer to as Gabriel's I-have-a-idea-that-will-end-with-Cas-in-tears face. It was the same face Gabriel had worn right before he gave Castiel a seventh shot of tequila the night before they graduated and told him that their professor was totally into him, and Cas should go hit on him. It was the face Gabriel had made right before he pushed Cas through the door at the speed dating event Gabriel had set up. There was the time Castiel had been detained by TSA for four and a half hours. There was also the time that Cas got the tattoo, and the time he drunkenly hit on a priest. All of those were preceded by the very face Gabriel was making as he crawled out onto Castiel's fire escape, a box of chocolates in hand.

“Whatever you are going to say, Gabriel, the answer is no,” Castiel warned as he looked down at the cat in his lap as though Balthazar could somehow save him from his friend.

“You can't say no before you hear my idea, and you won't say no when you hear it. I'm going to solve all of your problems, Cassie,” Gabe said assuredly as he lifted the bottle of wine and took a seat.

“You said that about the 'house keeper' you brought me. She turned out to be a Russian call girl with shoddy immigration papers, who you happened to be dating at the time. I'm sorry, but I would prefer it if you didn't try to solve any of my problems never mind all of them,” Castiel replied. Balthazar squirmed out of his lap as the tension built in his body, and the cat deserted him with a dismissive flick of its tail. “Traitor,” Castiel muttered under his breath.

“Cas, just listen to me. While Adler was in his meeting with the sponsors, I made a few calls,” Gabriel said as he opened the box and popped one of the truffles into his mouth.

“I suppose congratulations are in order for you actually doing the things you were hired to do,” Castiel deadpanned.

“Can it, pretty boy. What I'm trying to tell you is that I found out where Dean is having his bachelor party.” Gabriel couldn't hide the excitement in his eyes as he watched Cas carefully.

“You can't be serious? You want us to crash his bachelor party? That might be a new low, even for you, Gabriel.”

“You haven't heard the rest of it yet. I also happened to find out which agency is supplying the stripper,” Gabriel's glee may have actually been palpable in that moment. It nauseated Castiel just the slightest bit.

“Though I am afraid to ask, what does any of this matter, Gabriel?”

“Do you remember Meg? The private show I bought you for your last birthday?” Gabriel asked, his whiskey colored eyes alight with mirth.

“How could I forget the woman? She ruined the word dewy for me with her obscene dirty talk. Do you know how many times in the last seven months I have gagged while editing an article that describes the dewy nature of a primate's habitat?”

Gabriel's only reply was a shrug as he read the box of candy trying to find his favorite ones.

“Eleven times. What would even possess you to buy your gay friend a private dance with a woman? Are you secretly taking up my mother's crusade of turning me straight?”

“Well, I'm sorry if your birthday didn't fall on male stripper night. I was working with the available resources. And we are lucky it happened that way, because Meg is supposed to be stripping for Dean's bachelor party. However, I called up this afternoon and booked her for the day before,” Gabriel explained with a satisfied smirk, as though Castiel had followed any of his lines of thought.

“Why would you do that? What does any of this have to do with me?” Castiel couldn't hide the bewildered squint as he tried to puzzle out what Gabriel was trying to say, or what he was trying to avoid saying.

“We're going to pay Meg to stay home the night of Dean's bachelor party. Instead, you're going to go and wiggle those dangerously sharp hips of yours like Madonna in the 80s. Dean will realize what he's been missing all this time, and you'll not only get the man of your dreams but someone to pay that outstanding cable bill I saw on your counter. I know, I'm a genius, you don't have to say it, but you can, I won't mind.” Gabriel gave Castiel the look again, but Cas didn't notice.

Castiel squinted at Gabriel as though if he tried hard enough he might see the hamster scurrying in the wheel that Castiel assumed had taken the place of Gabriel's brain. “I'm not certain I understand,” Castiel said at long last.

“Which part don't you understand? I mean, it's pure genius!” Gabriel said then took a sip of the wine.

“The part where you think this is both plausible and something I would do. Ignoring the moral ramifications of what you have suggested, because we simply don't have the hours necessary to hash that out, when in the fifteen years that you have known me have you seen me dance or take my clothes off in public?” Castiel asked as he took the bottle of wine from Gabriel's hands and began to drink heavily from it.

“Cas, this is the man of your dreams we're talking about. Sometimes you've got to make a grand gesture, step outside your comfort zone.”

“Gabriel this is not like the time I hit on the priest without realizing he was a man of the cloth. This is knowingly trying to sabotage a man's wedding, his opportunity at happiness. This is knowingly ruining any possible good opinion Dean Winchester ever had of me,” Castiel argued. He looked around through the waning light in the alleyway below, because he couldn't look at Gabriel in that moment.

“Cas, did you ever think that maybe we didn't see Dean anymore after that night because you rejected him when he'd finally built up the courage to ask you out? That maybe he was embarrassed that he made such an ass out of himself that you had to practically carry him home and put him to bed?” Gabriel's words were softer now, no hint of the glee they'd carried before. Gabriel was never serious, and his suddenly sober tone was jarring.

“Why would I ever consider that? He didn't ask me out. He asked me if I was 'interested in going back to his place and having a good time.' Then he went so far as to invite you to join us in that good time. What part of that sounds like a date?” Castiel played with the label on the bottle, because he still couldn't look at Gabriel. He refused to let Gabe see the sadness in his eyes.

“Like liquid courage never bit you in the ass,” Gabriel huffed.

“Why are you suddenly pushing this angle? Dean and I haven't seen each other in eight years. Even if what you're suggesting was the case, which it isn't, I'm sure we are both very different people now,” Cas said as he rested his head in his hands.

“Cas, I'm your best friend. It is my sworn duty to have your back—morals and laws be damned. If I think my friend has a shot at happiness, then it is my job to make sure he takes it even if it might hurt a little,” Gabriel said as he patted Cas' back with a steady hand. “So, Friday after work, be ready to spend some quality time with Meg, because if all goes according to plan, she's going to be giving you a crash course in how to be a stripper. Now get some rest,” Gabriel said before slipping through the window again.

Castiel sighed as he rubbed tiredly at his eyes. This was not how he imagined his life would turn out when he was in college. Maybe he hadn't expected a white picket fence and a dog, but he certainly hadn't pictured this either. Castiel groaned as he got to his feet. No amount of protests or threats would dissuade Gabriel. He hadn't gotten the nickname the Trickster for nothing. Castiel just hoped that Gabriel would lose interest in this before it came to fruition, or that Cas, himself, got struck by lightning before he could ruin his life and reputation to the beat of some bass heavy dance pop.


	2. Unwelcome Thoughts

**Notes for the Chapter:**

> You get a look at Dean's life in this chapter. I'm sorry if there are any typos, but I wanted to get this out before I had to go out this evening. To be fair, my hair is shoddily straightened, because I was paying more attention to editing.

“You hired Meg? To strip for the party? Crazy Meg?”

“Yeah, the one who wants to wear you as a second skin. She's giving us a discount if she gets to give you a lap dance,” Dean replied as he waggled his eyebrows. Sam looked horrified. If it was possible, Dean suspected that his brother's hair would have puffed up at the affront like a disgruntled bird. 

“Why would you do that, Dean?” Sam asked as he helped his brother load the Impala with decorations they had picked up for the wedding. “She sat in my lap and refused to move until we put nearly a hundred and fifty dollars in her bra, all the while saying some of the most ludicrous things I've ever heard. That's saying something since you raised me.”

“Well when my brother got on his moral high ground and refused to hire strippers for my bachelor party, I had to take matters into my own hands. If you had hired the entertainment, like a best man should, you could have hired anyone you would like. Hell you could have hired a dude just to mess with me, but you gave up the right to complain when you said you wouldn't help,” Dean replied with a complete lack of sympathy for his brother. The Impala was brimming with boxes and bags of wedding supplies. Since Lisa was an event planner, she had insisted on doing everything herself, something about dream weddings. Dean shook his head as he looked at his Baby, but Sam pulled his attention back.

“I'm sorry that I wanted to avoid a repeat of _my_ bachelor party,” Sam grumbled as he shoved a box into the truck a little harder than necessary. 

“What are you talking about? Your bachelor party was great,” Dean said. He was offended that his brother would complain about a party that took him three weeks to plan and possibly an equal number of weeks to recover from. It had been the most epic party ever, complete with party bus, strippers, and more alcohol than they could possibly drink.

“Dean, you hired two strippers for my party, the angel and the devil. Then you slept with both of them and were almost late to the ceremony. I just thought it prudent not to repeat that incident for your wedding,” Sam gave a patented bitch face as he rounded on his brother. Dean at least had the decency to look sheepish.

“First of all, I got to the church on time, and I was a damn good best man. I didn't even tell Jess about how you cried like a little girl before the ceremony started. As for the girls, it was five years ago. I don't do that anymore. Lisa's been good for me, and I'd never cheat on her,” Dean defended himself.

“I know you've grown up a lot, Dean...”

“Yeah, yeah, Samantha. Let's not get weepy,” Dean said as he slipped into the driver's seating.

“Jerk.”

“Bitch,” Dean slung back as he started the car and drove them back toward the house he shared with Lisa. 

They spent the majority of Friday morning and into the afternoon doing exactly what Lisa and Jess told them to, for fear of what would happen if they didn't. Lisa was by no means a crazy bride, but neither Dean nor Sam wanted to test her limits. Dean was relegated to place marker folding, because he outright refused to make bouquets with the girls. Sam had no such compunctions having been through this once already. Dean started to wish he had agreed to play with flowers after he received his fourth paper cut in the last twenty minutes.

“Lis, you want me to pick up Ben, so you girls can finish up?” Dean asked though he looked pointedly at his brother. Sam rolled his eyes at Dean's unoriginal barb.

“Don't pick on my husband, Dean Winchester. I have it on good authority that you get teary during _Ghost_ ,” Jess piped up before Lisa or Sam could reply. 

“That doesn't count, Jess. Everyone cries during _Ghost_. Swayze is king,” Dean defended as he sent his brother another disgruntled look. “By the way, Sam bawled like a baby before your wed...”

“Dean!” Sam shouted at his brother as he wrapped the bouquet in his hands just a little too tightly. “Real mature.”

“Serves you right for telling Jess that I cried during _Ghost_ ,” Dean snarked as he looked around for his car keys.

“Jo was actually the one that told me, and let's see how dry eyed you are come Sunday,” Jess said triumphantly. Dean bit his lip and shrugged at his brother. Sam shook his head and went back to what he was doing. In all honesty, Jess was well aware of how emotional Sam was before, during, and after their wedding ceremony.

“It would be a great help if you got Ben. Thank you, Dean,” Lisa answered when they were finished arguing. She smiled at him sweetly as he walked around the couch to kiss her softly over the back of it.

“We'll pick up the tuxes on the way back,” Dean said as he pulled away, smiling down at his future wife. He ran his fingers through her hair to push it out of her face then dropped a quick kiss to her forehead.

“What did I ever do to deserve you?” Lisa asked as she smiled up at him.

“Probably something really awful,” Sam muttered and received an elbow to the ribs from his wife. 

“See you later, babe,” Dean said ignoring Sam's remark, then he walked back around the couch, slapping Sam upside the head as he went.

“It's hard to believe the playboy I hooked up with in undergrad would turn out to be such a considerate and loving man,” Lisa said when Dean was gone. 

“You're telling me,” Sam agreed as he watched his brother slip into the Impala and take off out of the driveway like a bat out of hell. Sam and Jess had flown out from California two days earlier to help prepare for the wedding. Since their arrival, Dean had seemed off. Sam thought he was the only one that noticed, and even he wanted to write it off as nerves about taking such a big step. Since Dean had only been made partner two months prior, it was a lot of changes in such a short period of time. However, this seemed different somehow. Sam had been trying to find the right time to talk to Dean about it, but Dean had all his best defenses up. He kept picking stupid fights with Sam to deflect from any sort of meaningful conversation, and it had Sam worried.

***

Dean waited outside Ben's school listening to one of his Led Zeppelin tapes. “Ramble On” started to play, and Dean couldn't help but think about all of the things he'd been doing his best to ignore the past few weeks. All the while Dean grew up, he'd had one dream, and that was to take the Impala for one hell of a road trip. However, his dad had drilled into him that he needed an education, so he could get a job that he could be proud of. Dean had applied to college to appease his father, and he'd picked his major because political science had sounded like a joke. He'd never had any thoughts of becoming a lawyer until Anna and one of his professors had told him what potential he had. Anna had gone so far as to find and help him fill out nearly a dozen law school applications. Dean had done it for the sex she rewarded him with, but he never planned to send any of them.

Dean had actually been looking into the fire academy. He figured that becoming a fireman was as respectable a job as any, and he would actually be making a difference. He had a plan. He was going to tell Anna that it just wasn't going to work, then he would finally muster up the courage to tell Castiel – the blue-eyed nerd, he'd been in love with since the boy nearly ripped his towel off in the middle of the freshman dorm – how he felt about him. Then if he made it into the fire academy, he would still be close enough to see Cas with some regularity. However, when Dean woke up the morning after breaking up with Anna to a vacant bed, a pounding head, and a fleeting memory of being politely turned down by Castiel, he'd sent out all the law school applications and most of the meager savings he had in a fit of shame. He couldn't face Cas or his friend Gabriel after that, so when the first acceptance arrived, he started coming up with his ten year plan. Now, eight years into that plan, Dean felt stifled by his own ambition. He was just afraid to do anything about it, but moments like this with “Ramble On” playing made him wish.

“Hey, kiddo,” Dean said as Ben slipped into the backseat of the Impala. “Your mom's doing some wedding stuff with your aunt and uncle, so we've got to handle some errands. How's that sound?” Dean asked as he pulled the car away from the school. Ben readily agreed, and they were off to the tux shop. “Your mom's going to go nuts over you in a tux, man,” Dean said after he'd paid and they were carrying the clothes out to the car.

“Won't she be more excited to see you in one?” Ben asked as he looked up at the man who had essentially been his father for the last five years.

“Nah, mom's just get all weepy when they see their babies all dressed up. Just one of those things,” Dean replied. He laid the tuxedos out on the back seat then took Ben's and placed it on top. “Up for the front seat?” Ben nodded excitedly. “We'll keep this just between us,” Dean said as he unlocked the passenger door for Ben to get in, then he walked around to his side.

“They're probably still going to be busy with all the preparations until the rehearsal tonight, so what do you say we go hang out at the Roadhouse for a bit? Ellen will make you a burger, so you don't have to depend on whatever healthy garbage Lis and Sam thought up for tonight,” Dean said as he pulled away from the curb.

“Yeah. Will you show me how to play pool while we're there?” Ben asked excitedly as he watched Dean drive.

“I could do that,” Dean replied, taking his eyes off the road for a moment to smile at the young boy. He listened to Ben talk about school and his friends while he drove the short distance to the Roadhouse. The school year was just about finished, and Ben was already asking whether he could stay with friends while Dean and Lisa were on their honeymoon instead of with Ellen and Jo. Dean gave the patented “you'll have to ask your mother” response as they pulled into the empty parking lot of the Roadhouse.

They walked in to find Jo behind the bar hanging the cleaned glasses in the racks over the bar top. She smiled brightly at the pair as they each took a seat in front of her. “What are you two doing here?” she asked as she looked at Dean with a concerned expression.

“Dean doesn't want to play with flowers,” Ben answered with a smirk.

“Hey, I didn't even tell you they were making bouquets,” Dean said as he ruffled the boy's hair.

“You didn't need to,” Ben replied as he pushed Dean's hand away with a put upon huff.

“He's certainly got your number,” Jo laughed at Dean before pulling a beer out of the cooler beneath the bar. She put it on a napkin in front of Dean then looked to Ben. “What can I get you, big man?” she asked with a doting smile.

“Dean promised me a burger.”

“Did he now? How am I supposed to get ready for tonight if the groom is having me cook for him and his kid?” Jo turned to Dean with a sharp look.

“Joanna Beth, make the boy a damn burger,” Ellen shouted from the back room. Jo rolled her eyes and Dean just smirked at her. 

“Hey, Jo. Is Ash here?” Dean asked before she slipped into the kitchen.

“Yeah, he's in the back with Ma doing the accounts. Since we're closed for the night, seemed like a good time to get that done,” Jo said as she disappeared. Dean slipped around the bar and poured Ben a coke while Jo was making the boy some food, and Ben continued to tell Dean about his summer plans. He made Dean promise that he'd help him with his pitching for Little League, and soon Jo returned with a huge burger.

“You mind hanging out with Jo for a few while I talk to Ash?” Dean asked as he slipped off his stool. Ben just nodded as he stuffed his mouth with the cheeseburger that Jo had made. 

“You okay, Dean?” Jo whispered as he went to slip past her into the back. He nodded curtly before going to find Ash.

“Dude!” Ash exclaimed in greeting when Dean stepped into the cluttered office at the back of the bar. Ellen just rolled her eyes and smiled up at Dean. 

“Could I steal Ash for a couple minutes, Ellen?” Dean asked as he looked at the papers they had strewn about the available spaces. 

“Sure thing, Dean. I might as well get ready anyway,” Ellen said as she started packing up the files.

Ash grinned as he shut down his computer and followed Dean out to the back of the bar. “You need me to do something for the bachelor party, Man?” Ash asked as he patted Dean's shoulder. Dean sat on one of the empty kegs that sat out back and sighed.

“I need someone to talk to that isn't my brother and who knew me back in college,” Dean admitted as he looked down at his callus free hands.

“Well that does cut the list down, I guess,” Ash replied as he took a seat on a crate to Dean's right. “Well the doctor is in, so shoot.”

Dean put his head in his hands as he took a deep breath. “Do you remember that semester that we lived together after you'd come back from MIT, and I was about to graduate from KU?” Dean asked, but he didn't lift his face from his palms.

“Of course, it was like one long ass rager,” Ash responded with a fondness in his voice. “Actually, I haven't seen you look this serious and down since right before you broke it off with the Anna girl that semester,” Ash noted as he craned his head to get a better look at Dean. 

“Yeah, I thought I was going to marry Anna back then,” Dean sighed as he straightened up again. He kicked at a stone to avoid looking at Ash, waiting for the other man to piece together what Dean was failing to say.

“Nah, man. Anna thought you were going to marry her. I don't think you ever saw yourself getting married if our drunken heart-to-hearts were any indication. I don't remember much of those months, but I remember you telling me on more that one occasion about how you just wanted to say screw it, take your damn car, and just drive away. Start fresh somewhere. Then you dumped Anna, and we really thought you were gonna do it, man. Thought, I'd come back to the house after a party and find all your stuff missing,” Ash said as he pulled out a joint, seemingly out of nowhere. “But then we went to that party after the break up, you woke up the next day and actually sent all your law school apps that had been piling up. You never talked about doing your own thing again,” Ash said before lighting the joint.

“I don't know what I'm doing anymore, Ash,” Dean admitted as he accepted the joint and took a hit himself, something he hadn't done since they lived together.

“Is this because you aren't happy being a super successful suit with a hot soon-to-be-wife, or is it because you're still pining over that guy that you broke up with Anna for?” Ash asked.

Dean nearly spit out the beer he had been drinking at Ash's question. He'd come to Ash, because he'd been around back then and knew the guy Dean was, but he hadn't expected Ash to remember all those details. He certainly hadn't expected him to have pieced it together that Dean had been in love with a dude they only saw at frat parties, especially not back then when Ash was even farther out in space than he currently was.

“Don't look so shocked, Dude. You described the guys eyes as a storm at sea. There was no way you weren't in love with him. So, it's the pining then?” 

“I think it might be a bit of both,” Dean groaned. This was his life. He was getting relationship and life advice from a man who referred to himself as Dr. Badass, and who he was fairly certain had not been sober in the last decade. 

“Well, if you want my advice,” Ash paused to take a puff of the joint that he still held. He let the smoke out in a slow exhale before turning to look Dean in the eye. “I think that road trip is long overdue. Lisa's a great girl, and Ben is an awesome kid, but dude, marrying her isn't suddenly going to erase all of the things you're feeling right now. It's not fair to Lisa, and it definitely isn't fair to the kid,” Ash said reasonably.

“I really do care about Lisa,” Dean protested half-heartedly. “And Ben is like my own son.”

“Dude, just because you care about them doesn't mean you're ready to be husband and father to them. Hell, I love Jo and Ellen, but the thought of never having the freedom to disappear for a month without word again is something I can't handle. You're either marrying her because you love her and you see yourself as a family man, or you're marrying her because it's all part of the ten year plan. You have to decide which it is, but if it's the plan, do everyone a favor and take the road trip instead,” Ash said. He patted Dean's shoulder as he pushed himself to his feet and turned back to the backdoor. “I should probably go get ready for the rehearsal,” he said before leaving Dean to his thoughts.

Dean walked back into the bar proper to find Ben sitting in a booth listening to AC/DC on the jukebox. “They leave you to your own devices?” Dean asked annoyed that Jo had left Ben alone. Ben just shrugged as he played with the bar menu on the table. “Why don't we play a round of pool while they're all getting dolled up?” Dean asked with a small smile, and Ben beamed up at him. 

Dean showed Ben how to rack up and the proper way to shoot. They lost track of time as Ben devoured every bit of knowledge that Dean passed on to him. Jo, Ellen, and Ash came down after a few rounds, so Dean and Ben headed back to the house to get ready for the rehearsal. Dean played the music extra loudly as they drove to drown out his nagging thoughts.

**Notes for the Chapter:**

> Next chapter should be up tomorrow or the next day. Hope you're enjoying it so far!


	3. Learn to Dance

Castiel was mentally berating himself as he sat in his ancient station wagon, waiting for Gabriel to arrive at the dance studio he'd booked for them. Cas had gone to work that morning hoping against all odds that Gabriel had been joking, and he wouldn't have to go through with this crazy idea. However, there was a CD waiting for him on his desk when he had arrived. PLAY ME was written on it in messy handwriting. Castiel had hidden it in his desk drawer and pretended he hadn't seen it when Gabriel came to find him at lunch.

Much to his horror, Gabriel had brought another copy with him. This one was labeled, CAS' STRIPTEASE MIX. Cas had nearly shrunk under his desk at the thought that someone might see the CD.

“Come on, Cassie. You need the right music to get in the mood. This happens to be the perfect mix of tunes to get even you in a dancing mood,” Gabriel had said with such certainty that even Cas was slightly curious, but not curious enough to tell that to Gabriel.

Castiel waited for Gabriel to pull into the parking lot. He'd said he would be there at seven-thirty, but Castiel was used to his friend showing up over an hour late to things. His only hope was that Gabriel would arrive before Meg. Castiel wasn't certain he could handle Meg on his own. The woman may not have been more than five and a half feet tall, but she was frightening, even more so because she liked toying with Castiel.

At 7:53, Gabriel pulled up in his Camero. Castiel didn't know where all of Gabriel's money came from, and he was smart enough not to ask. If the cops came to ask him questions, he could honestly say he knew nothing, and he intended to keep it that way. Cas often wondered why Gabriel kept his job as Adler's assistant when he clearly didn't need the paycheck. Castiel wished that he didn't need every last penny of his own measly check.

“Cas, baby, why are you hiding in your car? Let's get this show on the road,” Gabriel called from where he rifled through the passenger side of his car. He was wearing a pair of aviators and the most ridiculous purple jumpsuit that Cas had ever seen. Castiel sank lower in his seat and begged whichever god he had pissed off to forgive him and not make him do this. “Don't be that way, I brought you something to wear too,” Gabriel shouted as he held up some iridescent blue fabric.

“I will not be wearing anything that you brought for me,” Castiel declared as he stepped out of his vehicle. He tried to smooth out his rumpled suit if only to hold on to what dignity he had left.

“The idea is that you don't wear anything, Cas, but there is nothing sexy about watching you fumble out of your slacks. You're going to need tear aways,” Gabriel said as he waved the dark blue material around some more. Castiel groaned as he slammed his door shut and followed Gabriel into the studio. This was going to be the most painful night of his life.

Castiel wasn't too far off. As soon as they walked into the dance studio, one of the instructors stepped out of the office with a seductive smile aimed straight at Gabriel. Her dark skin was highlighted by the blood red leotard and wrap she wore, and Castiel couldn't help the cold shiver that ran down his spine when she glanced at him.

“I was shocked when you called, Gabriel. I never expected to hear your toady little voice again,” the woman said in a deep velvety voice.

“Castiel, this is Kali. She owns the studio. Kali, this is Castiel, my best friend,” Gabriel made quick introductions, though his eyes were saying something completely different as he continued to look into Kali's eyes.

“A pleasure to meet you,” Castiel offered though he stayed behind Gabriel.

“If you are anything like Gabriel, I can assure you that the pleasure is all yours,” she said with a pinched smile over Gabriel's shoulder. “You can use the basement studio, but I swear that if you are doing something illegal, they will be finding your body parts for years to come,” Kali warned just loud enough that only they could hear, poking her deep red fingernail into Gabe's chest.

“Of course it's not illegal. I'm surprised you would think something like that.”

“You shouldn't be. I know you,” she replied as she ran the backs of her fingers down his cheek. “Don't make me regret answering your call,” she warned before walking back into her office. Castiel only noticed the inquisitive looks from parents and children alike when they turned to face the entire waiting area. Castiel heaved a sigh as he watched several mothers look his dirty trench coat up and down with deep set frowns. One woman even went so far as to shield her young daughter's eyes from Gabriel's risque outfit. He couldn't blame them, they were a couple grown men in questionable clothing meeting up at a dance school to get stripping lessons.

“I'm starting to think Kali and I have much in common,” Castiel said when Gabriel finally led them down to the unoccupied basement.

“Yeah? Well, don't get on that woman's bad side is all I can say. She'll ruin your fuckin' world,” Gabriel muttered as he pushed into the closet sized studio and turned on the lights. The room was not very large, but it was kept up just as well as the ones they had passed upstairs. The floors, though marked up from tap shoes, were in good condition, Two walls were lined in floor to ceiling mirrors. Castiel was immediately put off by his inability to hide form his own reflection.

Gabriel was looking through his duffel bag while muttering to himself when the door opened again. “Hey there, Clarence. Love the suit. Did you wear it just for me?” Meg said from the doorway. Her deep brown eyes looked him over hungrily. Castiel stood tall and threw his shoulders back. “Oh, going to get assertive on me?” she asked as she smiled widely. She stepped into the room carrying a bag of her own, and she stepped into Castiel's personal space. “I might even let you break the no touching rule if you keep looking at me like that...”

“Meg, step off,” Gabriel ordered as he stepped over to the pair and actually pried them apart.

“If it isn't the tacky little Trickster. I should have known something was up with this job. Lilith gave me no details, just said it was safe,” she rolled her eyes at Gabriel. “What do you want, Gabriel? I know for a fact that I'm not your type, and Clarence here practically cried the last time I was in his lap,” she asked as she crossed her leather clad arms.

“I'm leaving if this is one of your elaborate jokes, Gabe. My hair was an ungodly shade of green for a month the last time you were having fun at the club, so unless this starts with the world's most convincing and lucrative apology, I don't want to hear it,” Meg said as she turned to leave.

“Meggy, please just hear me out. It isn't for me. It's for our dear Cassie. He's in love with your bachelor tomorrow,” Gabriel called as she walked away, the heels of her boots clicking on the flooring. Meg paused just before she got to the door. “I know you hate me, but you're a romantic in the gooey black heart of yours. Just hear us out,” Gabriel pleaded. “I promise you'll get paid double.”

It was the money that made Meg turn around, and she will swear to that till the day she dies. It had nothing to do with the perpetually haggard looking man that stood two paces behind Gabriel. The swagger was removed from her steps as she walked over to them. “Make your proposal quick,” she demanded as she took a seat on the floor of the studio. Gabriel smiled widely as he seated himself in front of her and wasted no time in telling her about his plan. Castiel took to pacing around the room while Gabriel spoke. He never wished that he had admitted his feelings to Dean more than he did in this moment. Hearing Gabriel explain it to Meg, in plain words instead of the half truths he used to tell Castiel, turned Castiel's stomach.

“So, you want me to teach Castiel my best moves, so he can take my place at this bachelor party tomorrow and woo the groom out from under his blushing bride?” Meg summarized when Gabriel finally stopped speaking. Gabriel nodded enthusiastically, and Castiel rubbed his face in exasperation.

“You'll get whatever your cut is from the agency, and we'll double it just for staying home,” Gabriel assured her.

“What makes you think that Dean and party won't call the cops and my boss as soon as they see Castiel?” she asked with an arch of her brow.

“Because we've got something that Dean wants, obviously,” Gabe replied with an offended expression.

“And that would be?”

“Castiel's tight little ass!” Castiel and Meg both rolled their eyes at Gabriel's response.

“If I'm doing this, and I'm not saying I am, I want to hear from Clarence what's so great about Dean. Personally, I met the guy at the club a couple times, and he seems just like every other suit that comes in,” Meg said as she looked over to Castiel. “What makes you willing to risk utter humiliation for some guy you haven't spoken to in eight years?”

“I-I” Cas stuttered as he tried to put into words what he wanted to say.

“Meg, love is indescribable. You can't expect Cas to explain it,” Gabriel came to his aid, but Castiel stepped forward and looked at Meg with a tight smile.

“I suppose I was lost the first time I met him, but I don't think I really understood it until later,” Castiel began to explain as he recalled the year he had known Dean. While Gabriel still lived on Dean's floor, Cas and Dean had had a grand total of one real conversation. It had happened because Gabriel got held up in class, and Castiel was stuck waiting for him. Dean had come back from his own class and let Castiel onto the floor and even offered him a soda while he waited for Gabe. Dean's room had been covered in classic rock posters, pictures of classic cars, and pictures of half naked women on top of classic cars. However, right next to Dean's desk was a picture of a floppy haired kid holding a blue ribbon in front of what looked like a science project. There were a couple more pictures of the boy with Dean, and Dean had caught Cas staring at them.

Cas had been embarrassed and tried to apologize, but Dean had brushed it off and started telling Cas all about how smart his little brother was. In the twenty minutes that they spent together, Castiel learned all about Sam and his dreams of becoming a lawyer. He learned about Dean's desire to make his family proud, and that he was an RA to offset his own school costs, so Sam could have the whole college fund for his dreams. Then, Dean had done something incredible and asked Cas about his own goals. He'd even looked genuinely interested as Cas mumbled about his interests.

Cas shook himself out of his thoughts as he looked Meg in the eye. “Dean is one of the most intelligent and charismatic men I have ever met, but he is truly selfless and any occasion I had to speak to him he went out of his way to make me feel welcome and normal,” Castiel said with a nod. That was the best way he could articulate it, but there was so much more to it than that.

“That doesn't sound all that special, Sweet-Cheeks,” Meg said with a lopsided smile.

“Well, no one else has even done that for me,” Cas admitted as he took to pacing again.

Meg watched him for a minute with an oddly fond expression on her face. “Fine, I'll do this, but if this all goes to hell and bites me in the ass, I'm coming for your head,” she said pointing at Gabriel. “As much as I love the flasher look, Clarence, I hope you brought something else to wear,” Me said as she stood up and began to remove her leather jacket.

***

“No! You need to relax, or you're going to take Dean out instead of turn him on,” Meg said loudly as she watched Castiel attempt to do the warm up exercises she had showed him. “You know what? Forget it. Let's just start with the basics. If you pull something, you can't possibly look anymore awkward than you do already,” she muttered as she stepped behind Cas.  "I'm going to touch you," she said then waited for his nod before she laced her hands on his hips. Cas jumped forward at the contact, but Meg shushed him. “Not getting frisky, but it'll be easier if you let my hands guide you,” she said with a surprising level professionalism. “Now, move with my hands, and don't fight it.”

Meg moved her hands from side to side fluidly. Cas tried to follow, but his movements were much stiffer. Meg didn't make any comments but moved her body even closer to his so that they were pressed together. She slid her hands to the front of his hips and moved her own hips behind him to guide his movements. Cas stiffened briefly, but she squeezed his side and made her movements even more pronounced, until he had no choice but to follow her lead or fall over.

“Everything is going to come from your hips and your core. If you can't move them with any finesse, then there's no hope,” she said as he started to loosen up and get the hang of the sway of their bodies together. “It should be easier with music to guide you,” Meg said and nodded to Gabriel who had produced an old boombox to play his mix on. The music blared to life which spooked Cas enough to step away from Meg. “The Eurythmics, really?” Meg asked as she rolled her eyes.

“What? _Sweet Dreams_ is classic get-your-sex-on music,” Gabriel defended as he fiddled with the volume control.

“Try something a little slower, cowboy. Cas needs training wheels,” Meg said as she pulled Cas back in and started to sway her hips again. Gabriel obliged and put on a song with a slower tempo that Meg easily moved her body to. Castiel moved his with less ease, but by the end of the song, he was keeping up with Meg. “That's it. Now we're going to walk as we do this,” she said when the next song came on. She pulled Cas away from the ballet bar and toward the middle of the floor.

Cas took a steadying breath when Meg kept her space this time. It was back to just her hands on his hips as she instructed him to walk when she pushed him forward gently or step back when she pulled. It was unnatural to walk as he swayed his hips so exaggeratedly, and he stumbled when Meg continued to widen the sway.

“This is anything but comfortable,” Castiel remarked when she dragged him back to the start.

“Ain't supposed to be. Your body is a tool. You're going to use it to get at all the tight, sticky gears that you don't want to stick your fingers in. You turn Dean on, and you don't need to spill all those poorly articulated feelings you got bubbling around in there,” Meg said as she stepped around him and motioned for him to watch her.

“You make it all sound so easy,” Castiel said as he watched her. Meg walked toward him, one foot right in front of the other, with her hips swaying. When she was right in front of him, she stopped and stepped out so that she was standing with her feet hips width apart. She gave him a seductive look, popped her hip out to the side, then sank to a crouch with her hands on her knees. She did a small twist in that position giving him a bold view of the crotch of her leggings, then she came back up while swaying her hips. Both Castiel and Gabriel looked at her with wide eyes—Castiel's because he was impressed, and Gabriel's because he'd gotten that little show from the back.

“It _is_ easy. You just need to be comfortable with yourself.”

“If I was comfortable with myself, we wouldn't be here in the first place,” Castiel muttered, but Meg slapped him lightly on the chest.

“You're a smokin' hot man with soulful eyes and a hot body. If that isn't enough, you are putting yourself on the line for the man you love. I don't want to hear anymore negativity from you. Now, let's work on that move, so we aren't stuck here all night.

***

Two hours later, Cas' body ached in ways he had not known were possible. He was grateful that he was at least flexible, because Meg had contorted him into some interesting positions under the claim that they looked “hot.” She had guided him through everything with a level of patience that was impressive, especially when Gabriel felt the need to comment every few minutes.

“Okay, I'm going to pick a song, and you're going to do the moves I've shown you. Start with the walk, make eye contact then pose. Then take it from there,” Meg instructed as she pushed Gabriel away from the boombox and flipped through the available CDs. _Like a Prayer_ came through the speakers, and Gabriel took his turn to roll his eyes. “Don't start,” Meg warned then gave Cas the cue to move when the intro finished.

His movements were not completely natural looking but he walked forward and moved his hips with each step. He looked nervously at Meg when he stopped to pose with his legs spread and hips pushed forward. Meg smiled and nodded encouragingly as he slowly sank to his knees and thrust his hips forward as he knelt on the floor. His movements were a bit jerky as he tried to push back on his heels to come up again. He ended up losing his balance and falling on his ass. He huffed in embarrassment while Gabriel laughed at his complete lack of coordination.

“That's okay. You don't want to know how many bruises I got when I was getting started,” Meg said as she paused the song. “You don't have to come up from that the way I do,” she said as she crawled over and knelt beside him. She thrust her hips forward while throwing her left arm over her head and her right behind her to support herself. She pumped her hips a couple more times before dropping her left arm to the ground between her knees and shifting up and forward. She used her arm to support her weight as she came up, until she was bent over with her ass in the air as she continued to move it enthusiastically. “Why don't you try that instead?” she offered as she straighten and stretched out her hand to help him to his feet.

“Why don't I just go home and drink until I forget all about this and Dean Winchester?” Castiel asked as he wiped off the sweatpants that Gabriel had given him to wear.

“No negativity, remember?” Meg scolded as she pushed him back to the start and replayed the song. After ten run-throughs of the steps Meg had taught him, Castiel could make it from start to finish with only minor stumbling and without looking like a robot attempting to dance. Gabriel had disappeared at some point with some half-assed excuse about getting a cigarette even though he didn't smoke. “Okay, now you need to learn how to take off your clothing while you're doing all this. This should be the easy part since most of the clothes Gabriel has for you are tear away,” she explained as she walked over to Gabriel's duffel bag and started pulling skimpy garments out of it. She held up a very small pair of blue spandex booty shorts.

“I will not wear that,” Castiel said firmly, but Meg just shook her head at him.

“It's just you and me here. Unless you want it all hanging out, you need something to wear under these pants,” she said as she held up equally tight looking blue pants.

“No, thank you.”

“I didn't just spend close to three hours showing you how to walk without looking like you have a stick shoved up your ass just for you to dip out now. So, either put on this admittedly ridiculous outfit, or pay me so I can go home,” Meg said as she threw the clothes to him. Castiel sighed as he picked up the tiny garments off the floor. “Good boy. I'll go see what Gabriel has gotten up to while you change,” she offered as she walked out of the studio.

Castiel was desperately trying to adjust his balls into a comfortable position in the tiny shorts when Meg stepped back in. She laughed at the picture of him with his hand shoved down the extremely tight pants. “From what I'm told, there is no comfortable position until you get used to it. I'll make this as quick as possible if you follow along,” she said as she turned the music on again. She picked a song with a rhythm that he could follow, then she stood beside him.

“Okay, there are several different schools when it comes to stripping, but seeing as you have trouble walking in a straight line while swaying your hips, we're going to keep this simple. The goal is to get your clothes off while doing it in a teasing and enticing manner,” Meg explained as she straightened his clothing a little.

“I have watched a stripper before. I think I understand the process,” Castiel said offended. Meg slapped his chest again and told him to let her teach.

“Okay, so we'll start with the shirt. Pop the snaps as you do the walk forward, then when you get to the part where you pose, you're going to open your shirt completely.”

Castiel fumbled through her instructions the first few times. When he finally got the timing and the movements correct, he turned to Meg proudly. “Where was your eye contact? I think the floor might be really turned on right now, but I'm not,” she burst his bubble and sent him back to the beginning.

It was nearly midnight when Gabriel and Kali came back down. Both of them looked disheveled as they stepped through the door to find Castiel in nothing but the shiny blue booty shorts kneeling in front of Meg with his crotch in her face. Castiel disappeared behind a stack of chairs in the corner before anyone could make a comment.

“How's the student?” Gabriel asked as he stepped into the room. Kali followed him warily as she looked at the clothes strewn about the floor.

“He's passable considering what we had to work with and the time limit,” Meg said as she gathered the sweatpants Cas had begun the lesson in and brought them and his t-shirt to him behind the chairs. Castiel stepped back into sight when he was fully dressed and sent Gabriel a dirty look.

“Great because Kali's kicking us out. Well, she's kicking you out so we can go... ow,” Gabriel said as he rubbed his ribs where Kali had hit him.

“That's fine,” Meg said as she quickly gathered their belongings. She and Castiel walked out to their cars side by side, both exhausted.

“Thank you for your time and patience, Meg,” Castiel said when they reached his vehicle. “I am sorry that I was neither a willing nor an apt pupil.” He looked down at her, and she smiled up at him.

“Don't worry about it. Gabriel paid me enough to make it worth while,” she brushed it off. “Do you have the list of clothes that Gabriel needs to buy you and the name of the songs to dance to?” she asked, and he nodded. “Good. You're going to do fine tomorrow. Don't stress yourself out too much. If Dean's into you, it won't matter if you trip all over yourself or fall flat on your face. The fact that you want to take your clothes off for his pleasure will trump any slip ups you make,” she assured him with a gentle pat to his cheek.

“And how will I know that?” Cas asked solemnly.

“You'll see it in his eyes, you nut. Why do you think I drilled eye contact so much?” Meg asked with a smile. “And I don't know many people who wouldn't be into you, Clarence. Now, go home and get some rest,” Meg said as she rose to her toes and placed a kiss on his cheek. She walked away before he could reply. Castiel unlocked his car and sank into the driver's seat. He wasn't sure he'd be able to walk tomorrow because of this lesson, never mind dance.  

**Notes for the Chapter:**

> I had every intention of getting this chapter out last night, but then it turned out to be twice as long as I'd originally imagined it would be. You can also find me on tumblr under the username jinxedambitions.


	4. Is This Even Clothing?

**Notes for the Chapter:**

> I wrote this chapter out today, and it turned out to be over 5,000 words. That just seemed a bit excessive, so I cut it in half, and you have a bit of a cliff hanger. Sorry, friends. The good news is that the second half is already written, so it'll be up sometime later today since it's already after midnight.  
> Anyway, hope you enjoy.

Gabriel arrived at Castiel's apartment at 3PM on Saturday, carrying several large bags. He let himself in, knowing there was the possibility that Cas would lock the deadbolt instead of letting him in if he chose to knock. “Cassie, I come bearing gifts!” Gabe called as he swept into the apartment. The only reply he received was a meow from Balthazar who watched him from the back of the sofa. “None of it's for you,” Gabriel told the cat as he walked past the animal toward Castiel's bedroom. 

As he got closer, he heard the shower running. That explained Cas' absence, so Gabriel snuck into the room and laid out all of the garments that he bought for Cas on the bed. Then he went back to the living room and watched a rerun of Dr. Sexy until Cas was finished. Doctor Sexy and one of the new interns were just about to slip into the supply closet when Gabriel heard shouting coming from Cas' room. He couldn't make out what his friend was saying, but he shared a knowing look with the cat before he pushed Balthazar out of his lap and wandered toward the bedroom.

“What is all of this?” Castiel demanded when Gabriel slipped into the room. Castiel was only wearing a towel, but that was definitely more than he would be wearing that night, so Gabriel shrugged it off. 

“It's what was on the list you emailed me,” Gabriel said with a shrug as he lifted up the lacy blue garter belt that he'd purchased not an hour earlier. The lady at the register insisted it was the perfect gift for his lovely lady, and wouldn't she love to have a man buy her such a beautiful garment. He just wasn't going to tell Cas that.

“I... _This_ is woman's clothing!” Cas exclaimed as he picked up the fishnet stockings with a baffled expression.

“It's only woman's clothing if a woman is wearing it, Cas. Clothes aren't sentient. They don't decide who gets to wear them,” Gabriel said as he rolled his eyes. “Cas, just try the stuff on and see how it looks. You've got to be there in eight hours, so I really don't have time to walk you through a crisis where you question your masculinity. You're six feet tall and could beat me to a pulp without much effort. Wearing a pair of satin panties and some fishnets is not going to change that.”

“It's not that. Just...what if he thinks I'm strange?” Cas' voice was softer, and he looked like Balthazar had just gotten kicked. Gabriel rolled his eyes.

“Cas, you are strange. You've had men and women throwing themselves at you for years and haven't noticed. Hell, you had Dean Winchester throw himself at you, and you didn't bite. You named your cat after one of the three wise men. You practically run the magazine, but no one knows your name other than me and Adler. Cas, you're a weirdo, but I think if Dean remembers you, then he already knows that. So, buck up and put this stuff on, so I know whether I have to run back to the store for a different size,” Gabriel said as he laid the garter belt back on the bed and left the room. “Oh, and I expect you to show me when you've got them on. I don't trust your judgment,” He called over his shoulder as he firmly shut the door.

Cas took a deep breath after Gabriel left him, and he inspected the garments that Meg had insisted he wear tonight. At least the pants and shirt resembled the suit he wore to the office daily. It was only a small comfort though when he inspected the rest of the pieces. He could deal with the fishnets; they were actually quite silky when he rolled then up his legs the way he'd seen his mother do it when he was a child. 

The real problem was the the tiny scrap of stretchy blue satiny material that was supposed to pass as underwear. Castiel was not really an adventurous guy. He'd been wearing the same brand of boring white boxers since he was in high school. He held up the panties and gave them a harsh look wishing that his stare alone could add at least another square foot of fabric to them. It was not to be, so he took a deep breath and put his feet through what he thought were the leg holes. Nope, that wasn't right. He tugged them off and scrutinized them before trying again. This time, he pulled them up over the stockings, and it actually felt rather nice. 

He considered getting used to this, until the panties reached the top of his thighs and he had to coax his penis into the tiny pouch at the front of the underwear. He glanced at himself in the mirror on the back of the closet door, and he hung his head at how obscene the shiny bulge of fabric looked nestled right above the lacy top of the fishnets. He was never going to live this down, even if everything worked out, and Dean was interested in him. He would forever be Castiel: the man who wore a blue satin thong with fishnets and a matching tie to seduce his college crush. Castiel decided, as he fumbled to attach the straps of the garter belt to the stockings, that if he survived this night without dying of mortification, he was going to find himself a new best friend. Or maybe, he would just take in a couple more cats and forget about people altogether. 

Cas looked in the mirror again when the garter belt was attached over the panties. “Okay, at least that covers a bit more,” he muttered, but then he turned around and saw that pretty much none of his butt was covered. “I'm going to get arrested,” he said as he took a couple breaths. He quickly pulled the slacks and white snap up shirt on. Then he let his usual blue tie hang loosely around his neck the way Meg had told him to. 

He stepped cautiously out of the bedroom and walked into the living room to find Gabriel holding a glass of wine above his head while the cat stretched to reach for it. “Balthazar has a problem,” Gabriel informed him. 

“Maybe if you didn't constantly taunt him with it, he wouldn't have a problem,” Cas said unamused. He'd nearly thrown Gabriel off the fire escape the night he caught him trying to sneak his cat some wine. He thanked God every day that Gabriel had neither pets nor children that depended on him.

“It all fits. Can I put my lounge pants on again, until I have to leave for this ridiculous venture?” Castiel asked as he spun around quickly for Gabriel to see. 

“Not the shirt and slacks, idiot. I know what size pants you are. The underwear,” Gabriel motioned for him to drop his pants.

“Really, Gabriel? You want me to take my pants off, so you can inspect how well the fabric of my underwear hugs my crotch?” Castiel asked with a raised eyebrow. Gabriel shrugged.

“Would you rather me make sure they're good, or accidentally flash your nuts to a room full of strange men? You should also make sure that your pants tear away without any problems, because that's not something you want to find out in the middle of your dance. Now, off with them,” Gabriel said as casually as a man could while asking someone they weren't intimate with to basically get naked.

Castiel didn't even want to think about that outcome. So he looked down at the tight, stretchy navy slacks then back at Gabriel. “How exactly do I get them off?” he asked seriously as he studied the pants.

“You never owned a pair of snap up pants?” Gabriel asked incredulously. He sighed as he got off the couch, taking his wine glass with him. He handed the glass to Cas, then he reached down, grabbed the fabric near where it would tear apart and gave it a firm tug. The pants came off easily, and Castiel stood there holding the wine glass with the tails of his shirt just covering his crotch.

“Oh,” was all that Castiel could think to say. Gabriel nodded then tore open the snaps on the shirt. Castiel looked dumbfounded as he stood with his shirt hanging open and his tie dangling down his chest like an arrow pointing to his barely clothed crotch. He was only startled out of his stupor when he heard the click of Gabriel's camera phone. “Gabriel!” Cas roared as he dove for the phone, but Gabe was too fast and darted out of the room. 

“Delete that picture this instant, or I'll never speak to you again,” Castiel yelled through the bathroom door, where Gabriel had locked himself inside.

“It is not wise to threaten the man holding the blackmail,” Gabriel called through the door. “I'll come out if you promise not to hurt me.”

“I won't hurt you, but you better delete that picture,” Cas said defeated.

Gabriel stepped out of the bathroom and made a show of deleting the image. Cas sighed and ran a hand down his face. “By the way, Meg has a real talent. It looks like all the clothes are the perfect size,” Gabriel said with a wide grin. Castiel just rolled his eyes, completely done with his friend antics.

***

Dean fastened the string of pearls around Lisa's neck while they both got dressed for that night. “You look stunning,” he said after kissing her neck right above where the pearls lay. 

“You don't look so bad yourself,” she replied as she ruffled his hair. 

“Hey, I just finished doing that,” he said as he tried to coax the strands back into place.

“Who are you trying to impress? The stripper? It's not like I'm going to be there. Anyway, I like it better this way,” Lisa said as she looked Dean over from head to toe. He was wearing a pair of torn jeans and black t-shirt under a sage colored button up. 

Dean rolled his eyes but didn't go back to the bathroom to fix his hear. Instead, he wrapped his arms around her and kissed her then messed up her hair as he pulled away. 

“You're a child,” she said with mock anger as she swatted him on the chest. They both heard Sam calling Dean from downstairs that they needed to get going. Lisa sighed and looked up at Dean seriously. “Please, promise me you won't drink heavily tonight. I know you've been hitting the Jack pretty hard since you made partner, but I'd really love it if you weren't hungover for our wedding.”

“Yeah, Lis. Don't worry, I'll behave,” Dean said before pecking her on the lips one more time before bounding down the steps to meet Sam. “Ben, be good for Ellen tonight, or you'll spend the honeymoon scrubbing floors at the Roadhouse,” Dean called as he slipped out the door behind his brother.

***

Cas and Gabriel pulled up to the restaurant at 10:45. It was a pricey place, and Castiel could feel his anxiety kick into full gear. They weren't even going to let him into this place. Who was he trying to kid? He had no business wanting Dean Winchester.

“Cas, stop thinking. Thinking isn't going to help you tonight, so put away that over powerful brain of yours and let yourself feel. If I could, I would get up there and dance for you, but Dean doesn't want to see me naked—”

“Who says he wants to see me naked? He's getting married! To a _woman,”_ Cas argued as he wrapped his trench coat closer to his body.

“That doesn't mean he's not interested in men, or you. Seriously, Cas. I would kill to look like you in that banana hammock. _Dean Winchester_ would probably kill to look like you in that. So, don't be nervous. If shit gets weird, just play it off as the agency sent the wrong dancer. No one's first thought is going to be that you snuck in there to do a striptease for your college crush. Even _I_ wouldn't think that one up. So, get out of my damn car and go win yourself the man of your dreams,” Gabriel said as he patted Castiel on the shoulder firmly. When Castiel still didn't move to get out of the car, Gabriel gave him a hard shove which sent Cas right out of the already cracked open door. “That's better,” Gabriel said smugly as Cas rose to his feet and dusted himself off, never tearing his glare away from his friend.

“Hey, Clarence, wasn't sure you'd actually show up,” Meg said as she sauntered out of the shadow of the building, her hands tucked into her back pockets. 

“What are you doing here, Meg?” Cas asked as he pulled his duffel bag out of the foot well of the passenger seat and straightened up again.

“Well, I had to make sure you showed. The only thing worse for me than the wrong person showing up is if no one shows up. _And_ , I figured that you might need someone to do the talking, because you certainly don't talk like a stripper,” Meg said with a shrug of her shoulders.

“What exactly does a stripper talk like?” Castiel asked in confusion. He'd never thought strippers spoke any differently than anyone else he met.

“They can say the words striptease and lap dance without blushing, and they can negotiate how much a private dance will be without stuttering. Can you do that?” she asked with a sharp look.

“No, I suppose I do not have much practice with those sorts of things,” Castiel admitted. Meg nodded, tossed her hair over her shoulder, then walked to the front entrance where the doorman waited. Cas quickly followed behind her and listened with great attention as she easily told the man that they were the entertainment for the Winchester party. The doorman looked them both over from head to toe with a leer before nodding and giving them directions to one of the private rooms in the back.

“Do people always look at you that way?” Castiel asked as the walked through the fancy restaurant. No one gave them a second glance.

“Like what, Clarence?”

“Like they are picturing you with your clothes off.”

“I'm a stripper. Of course, they do.”

“But—”

“Yeah, it sucks a lot of the time, but you get used to it. You want to get paid; you don't start shit over stuff like that. They get handsy, then we have a problem,” Meg said sharply as she slipped into the employee section of the private room. She waved to a waitress who was bustling back toward the kitchen with a tray of empty dishes. 

“Okay, I've been here before. There is a small stage area that they set up for these parties. You're going to step through that door, then the stairs to the stage will be on your left. I'll start the music when you get to the center of the stage. Then you just do your thing. If shit goes bad for some reason, I'll run interference. _Don't worry_. I've got your back, and remember, Dean's going to be so excited that you're taking your clothes off for him that he isn't going to notice if you falter. Now, take a deep breath,” Meg said when she realized that Castiel was starting to look a bit blue in the face.

Cas took several deep breaths before relaxing his shoulders. Meg smiled encouragingly at him then went over to the sound system to set the music up. The waitress came out of the kitchen and smiled at the pair. “Hey, Meg. Should I tell the party that you're about to start?” the petite woman asked with a kind smile.

“Sounds good, Rachel. This is Clarence, by the way,” Meg introduced as she adjusted the volume of the system.

“A pleasure to meet you,” Rachel said as she held out her hand to Cas. He took it and returned the pleasantry. Then Rachel hurried into the private room.

“Clarence isn't my name,” Cas said once she was gone.

“You never use your real name in this business,” Meg said as she finally turned away from the system. “Not gonna tell you,” she said when he sent you an inquisitive look. “Now, deep breath, and get out there,” she said as she pushed him through the door. 

“ _Gentleman, please welcome your entertainment for the evening, Clarence the blue-eyed angel!_ ” Meg's voice came through the speakers as Cas stepped up onto the stage. The stage area wasn't lit yet, so he could see everyone in the room without bright lights shining in his face, and there were _a lot_ of people.  


	5. On With The Show

**Summary for the Chapter:**

> Castiel's performance does not go exactly how it was planned.

**Notes for the Chapter:**

> Chapter Warning: Someone has a panic attack in this chapter. I understand if that may be triggering or just something you don't want to read about. About the last third of the chapter is safe to read and will give you all the information you'd need going forward. It's marked by the only *** in the chapter.
> 
> I meant to get this out earlier, but I've been sick all evening. I'm sorry if there are more mistakes than usual. I did edit, but I'm kind of miserable, so I may have missed some stuff.
> 
> That being said. I hope you enjoy this chapter.

There had to be thirty men in the room wearing everything from full suits to one man in a plaid shirt with cut off sleeves. They were all crowded around Dean. Dean, who even from a distance, hadn't changed a great deal in eight years. He looked so comfortable in torn jeans and a t-shirt that it was hard to believe he was a powerful lawyer. And everyone flocked around him smiling and laughing, until Meg announced Cas.

Then the room got quieter, and everyone looked confused as the music came on. “I thought you said you hired Meg?” was the last thing Cas heard before the music drowned out the room and the lights came on, blinding Cas for a moment.

The first bars of _Like a Prayer_ played as Castiel stood frozen on the stage. He managed to shuck his trench coat as Madonna started to sing. He took a deep breath and walked toward the front of the stage. He kept his eyes on the crowd even though it only made his anxiety intensify, and he moved his hips the way Meg had showed him. He could do this. He was going to do this, and Dean was going to enjoy it, dammit!

Cas reached the front of the stage and tore open the last few buttons of his shirt.

Then the CD skipped.

Madonna stuttered over the chorus just as Dean stood up, “Cas?”

Just like that Castiel froze, and he felt his whole body seize. Oxygen was no longer an option, his chest was suddenly so tight that he was certain his heart might explode, and his stomach dropped so fast that it sent his lunch rushing up when it bounced back.

The skip smoothed out and the music continued, but Cas could do little more than stare at Dean who looked so confused and something else he couldn't place, probably anger. Probably more anger than he'd ever seen a human have written on their face, so he couldn't readily recognize it.

The small miracle was that Cas' tunnel vision prevented him from seeing all of the other angry and confused faces. Reality came swooping back in, and Cas ran. He jumped off the stage and sprinted back out of the room and into the bathroom they'd passed on the way in. He barely made it into an unoccupied stall before he was on his knees retching.

“What the hell was that?” Sam asked angrily as the group of family, friends, and coworkers watched the weird man rush out of the room.

“I thought you said there was going to be a woman,” one of the other partners from the said skeptically.

Dean didn't answer any of their questions. He just followed Cas out of the room. It couldn't really have been Cas. There was no way fate could be so kind and so cruel to him the night before he was to be married.

Meg stood in the hall with her arms crossed over her chest, and a smirk on her face.

“I don't know what your game is, but get out there and distract them, and make sure the waitress never lets their drinks get empty,” Dean growled as he stalked right past her to the bathroom.

Meg saluted his retreating back then marched out to the party of befuddled men in her regular work outfit.

Dean didn't spare her another glance as he pushed into the bathroom. His ears were immediately met by the sound of heaving, and he easily found the stall Cas was in. The man didn't even notice his presence as Dean knelt behind him and gently rubbed his back. Between bouts of dry heaving, Dean could hear Cas gasping for air which was only making matters worse.

“We need to try to steady your breathing. It'll help,” Dean said, and suddenly Cas was staring right at him, looking scared as well as ill. “Hey, I know it doesn't feel this way, but you're safe. It's just us, and I'm not going to let anything hurt you,” Dean said as he continued to rub Cas' back soothingly. Cas was still hyperventilating, but he was focusing on Dean without looking ready to bolt.

“Cas, listen to me. You're having a panic attack. I can help you calm your breathing, if you do what I do,” Dean spoke slowly and her measured his tone. When Cas nodded frantically, Dean stood up and helped Cas to his feet so they could get out of the stall. They sat on the tile floor in the middle of the bathroom, and Dean explained how they were going to count their breathing, and helped Cas through it as he continued to rub Castiel's back.

Eventually, Cas' breathing evened out, but he felt woozy and drained.

Dean got a fistful of paper towels out of the dispenser and dampened them with cold water. He sat back against the bathroom wall and motioned for Cas to either join him or sit beside him. Cas hesitantly leaned back against Dean's chest. Dean pressed a couple of the towels to the back of Cas' neck which was lathered in sweat. Then he put a couple on his overheated forehead. He placed his hand lightly over Cas' chest as made sure he was breathing steadily then removed it so as not to crowd him.

Cas groaned as the fear continued to dissipate. “Don't rush it. You're safe,” Dean said quietly in his ear as he massaged Cas' shoulder with his free hand.

“What happened?” Cas asked as he tried to sit up but ended up falling back against Dean's chest again.

“You had a panic attack, man, but you're going to be okay,” Dean tried to be as soothing and positive as he could be. He remembered his whole first year of being a lawyer. Before his first solo case, he found himself in the bathroom at the courthouse having a panic attack. He had learned every meditation and breathing technique in the book after that.

Cas seemed to realize it was Dean behind him right before his breathing went erratic. “No, don't do that. Breathe deeply with me. You're safe,” Dean said again before breathing in deeply.

“I'm never speaking to Gabriel ever again. Cats. I'll just get more cats,” Cas groaned as he finally seemed to release some of the tension in him and almost melt into Dean.

“Gabriel's still getting you into trouble, huh?” Dean asked with a fond laugh.

“You have no idea,” Cas said as his head lolled to the side so he could look up at Dean.

“Panic attacks will really take it out of you,” Dean said as he looked down into Cas' pale face. “We should get you some water or Gatorade. Get some color back in your cheeks,” Dean suggested as he pulled the paper towel away from Cas' forehead.

“I don't think I've ever been so embarrassed in my entire life,” Cas admitted, the deep timbre of his voice was coming back.

“Dude, you don't need to feel embarrassed. I used to get them before a case. I'm not judging,” Dean said as he patted Cas' back. He helped him sit up then scooted out from behind him. Wait here, I promise I'll be right back with something for you to drink,” Dean said as he slipped out the door.

He wasn't gone more than a minute before he stepped back in and locked the door behind him. “We've got water and orange juice, because they don't have any Gatorade,” Dean said as he sat down cross-legged in front of Cas. Castiel took the glass of water gratefully. He drank it with slow sips, and it helped to calm some of the residual tension that he felt. He mostly just felt exhausted now.

“You aren't angry with me?” Cas asked skeptically as he finished the water. He placed the empty glass beside him on the tile floor. He had to say, if he had to get sick and lie on a public restroom floor, he picked the right one. This bathroom was better kept that his own, and he was pretty meticulous.

“Nah, I'm more confused and worried than mad. How are you feeling?” Dean asked as he reached out and pressed the back of his hand to Cas' forehead.

“Tired. Embarrassed,” Cas admitted as he looked down at his lap.

“Yeah, they’ll do that to you. You mind if I ask you how you've been doing since college?” Dean asked as he placed the glass of orange juice between them.

“Oh um...” Cas trailed off not really knowing what to say. He hadn't actually planned for the slim chance that he would speak to Dean.

“It's okay if you don't want to talk about it. I know some days I wish I didn't have to talk about what I do, but that's all people seem to care about,” Dean admitted. Cas looked up quickly at Dean's words and saw understanding in his green eyes.

“But you are a—”

“Partner with Meadows, Larkin, and Larkin. Yeah I know, Cas. I'm also a guy who loves pie and classic cars, but no one really cares about that. My own brother and best friend got cake for tonight. Cake!” Dean said incredulously as though it was inconceivable that someone would buy a cake for a party.

Cas laughed. “I remember the time you left your birthday pie in the common room fridge, and Gabriel ate it. I thought you were going to explode; your face was so red,” Cas laughed at the memory and surprisingly Dean did too.

“Gabriel was the worst. He stole my jar of lollipops the first week of classes and then tried to tell me they were actually his every time I caught him with one,” Dean said as he rubbed at the back of his neck. This started a lengthy discussion of all the trouble Gabriel got into during college and since then.

Dean's easy way of making conversation, and the fact that he didn't ask any damning questions relieved more of pressure in Cas' chest. Eventually, the last night they ever saw each other came up and they both got quiet.

Cas took a deep breath and decided that it was now or never. “When you propositioned me that night, I was so excited,” Cas admitted as he kept his eyes firmly planted on the tile to the left of his shoe. “But you were so very drunk, and I just assumed that you were willing to sleep with anyone just to get over the breakup. And I didn't want to take advantage of that. Gabriel seems to think that we didn't see you anymore after that, because I inadvertently shot you down. That obviously wasn't the case because I mean, we made sure that you got home safe. I even made sure you had water and aspirin when you woke up,” Cas rambled.

“Well, Gabriel may be a thief and a trickster, but he is observant,” Dean said with a self-deprecating laugh.

“You can't be serious.”

“I had it so bad for you, but I'd never felt that way about a dude before. I broke up with Anna, because I really wanted to try with you. But I was super nervous, and I got so drunk then made an ass of myself. When you shot me down, I didn't have the balls to try again,” Dean admitted as he too stared at the tile floor. “I guess we're both dumbasses.”

“I don't even know how to respond to that. I spent the last eight years thinking I was crazy for even having feelings for you.”

“And I spent them thinking I was an idiot for loving a guy who didn't give two shits about me,” Dean laughed, though there was no humor in it. “So, let me guess. Gabriel put you up to crashing my bachelor party and stripping?”

“He promised that no one would come to that conclusion,” Castiel groaned, but Dean grabbed his hand and squeezed it reassuringly.

“No one who didn't know Gabriel would come up with that,” Dean said as he looked into Cas' eyes when he finally looked up from the tiles. “You want me to drive you home, Cas? Maybe stop at a diner for some pie on the way?” Dean asked with a tinge of hopefulness laced around his words.

“But what about your party?” Cas asked in confusion as Dean helped him to his feet and held his arm out, just in case Castiel was still unsteady on them.

“Dude, this party is for them anyway. I had to hire the entertainment myself, and I can't even drink, because I made a promise to Lisa,” he said as he waited for Cas to button up his shirt and make sure he looked presentable.

“Oh, well then I think I would like that very much,” Cas agreed with a hesitant smile.

“Awesome.” Dean patted him on the back and led him out of the bathroom. He didn't even tell the guys that he was leaving. If Meg and Rachel were doing their jobs, the guys wouldn't even notice. They slipped out of the building, and walked over to Dean's Impala. Dean patted the sleek black car fondly before saying, “This is my last night with Baby. Lisa wants to get a mini van because it's safer.”

“I cannot see you driving one of those,” Castiel admitted as he opened the passenger door and took his seat. “She's a beautiful car,” he said and Dean smiled so brightly that Castiel couldn't help but smile himself.

They drove mostly in silence even though they both had so many questions for each other. Even so, it a pleasant sort of quiet, that allowed both men to gather their thoughts while classic rock played softly on the radio.

 

***

“Is this place okay?” Dean asked as they pulled into a mom and pop sort of diner that Castiel had never been to.

“I trust your judgment,” Castiel said as he reached for the door handle.

“Damn right you do. Best pie in the city, right here,” Dean retorted as he stepped around the car to Cas' side and motioned for him to take the lead.

A woman well into her thirties, who was heavy with child, greeted them as they entered. “Don't see you around enough these days, Dean,” she called over as they took a seat in a booth that had seen better days.

“Yeah, things have been hectic lately with the wedding and all,” Dean replied with the same friendly smile he offered everyone he came into contact with.

“And that fiancee of yours turns up her nose at grease and pie,” the waitress said with a knowing expression as she waddled over and put a menu in front of Castiel. “We've got pecan, raspberry rhubarb, and lemon meringue. Which will it be?” she asked as she turned to Dean.

Dean smiled so brightly that Cas had to pretend to read his menu for fear he'd never be able to look away from Dean's face. “You take such good care of me, Beth. Let's do pecan, but keep the rhubarb ready. We might be here a bit,” Dean said as he sent the woman a flirtatious smile.

“Don't you sass me, Dean Winchester, or I'll tell your friend here all those embarrassing stories from when you'd come in here drunk,” Beth said as she swatted him with a menu. “You know what you want, babe, or should I give you a minute?” She asked Castiel. Her expression was just as warm and caring as when she spoke to Dean, and it made Castiel feel good.

“Oh, I wasn't going—”

“He'll have a cheeseburger, and a slice of the pecan as well,” Dean interrupted, and Beth gave them both a knowing look. She promised to get right on their order, and told them to behave while she was in the back. Then she walked away with one hand supporting her aching back and the other drumming a delicate beat on her belly.

“How do you even know I like burgers?” Cas asked once she disappeared. He meant it to come out more sharply than it actually did.

“Dude, you waxed poetic about the merits of cheeseburgers one night when you were wasted. I was trying to study for a midterm, and all I could hear was you telling Gabe about how good the burger you were eating was. Some of your descriptions were down right pornographic. I don't think I'll ever forget that, and you need to eat something. You put a major strain on your body tonight,” Dean explained as he watched Cas with smiling eyes.

“Oh...I'm afraid you've seen me at all of my worst moments,” Cas admitted in a monotone voice that disguised the mortification he felt.

“Dude, you have no idea what I saw as an RA. Your burger fetish is nothing,” Dean said, but they lapsed into silence after that. Beth brought Cas' burger a few minutes later, then she brought over a huge piece of pie for Dean, complete with a scoop of vanilla ice cream.

“I know tonight might be a touchy subject for you, and you can tell me to stop at any time. But I just got to say, what you did tonight took balls, man. I mean, you were going to take you're clothes of for me,” Dean said as he couldn't think of a more eloquent way to put it.

“Yes, had I known that you would have spoken to me either way, I would have skipped the first two steps in this crazy scheme,” Castiel huffed in embarrassment. He chose to scrutinize the half filled ketchup bottle instead of meeting Dean's gaze. The ketchup bottle couldn't crush his hopes with a careless expression.

“No one's ever done something so...” Dean paused looking for the correct word, but Castiel had a few of his own.

“Weird, creepy, stalker-esque,” he listed in his usual deadpan.

“Hot.”

“Hot? You say that, but you didn't even see me naked. You likely would have changed your tune then,” Cas said with such certainty that Dean grabbed his hand which rested on the table between them. He shook it slightly to get Castiel to look at him.

“Dude, you like me enough to take your clothes in front of a room filled with strangers, just to let me know you want me. That's pretty hot, _and_ I saw your chest. You're _not_ a disappointment,” Dean said before taking a big bit of pie. Some of the ice cream dripped down his chin, and Castiel couldn't hold himself back from wiping it away with his thumb. However, Dean caught him in the act, and he leaned forward to suck the ice cream off Cas' thumb. They both shuddered at the intimacy of the act.

Cas' voice was quieter when he responded. There was less certainty in his words. “Most people would have me arrested for what I did,” he said.

“Most people haven't been pining away for you for close to a decade,” Dean said with a smirk. “Or maybe they have. I wouldn't doubt it if you break hearts regularly.”

“I assure you that if I do, it is completely unintentional. Gabriel tells me that I am oblivious to flirtations,” Cas admitted. He took a bite of his burger, and he had to admit he was very hungry.

They talked for hours in the empty diner. Beth would come by from time to time to refill coffee or pie when it was needed. They talked about everything from their successes to their most horrific failures, and everything in between. Dean even told him about the strippers from Sam's bachelor party, and Castiel mentioned the priest he had accidentally propositioned.

By 3AM, Castiel had nearly forgotten what brought them here. It seemed like they were in their early twenties again, just having a late night chat at the diner. Dean was still the animated man that Castiel remembered, as equally vocal about his loves as his hates. The conversation was so easy that Castiel didn't know why he ever thought he couldn't just talk to Dean. For a moment, he even forgot that Dean would be getting married in a matter of hours.

“Boys, I know you could keep puttin' away my pie, but honeys, it's three in the morning, and you should probably be gettin' on home before you fall asleep here,” Beth said as she wiped down the bar area.

Just like that the fantasy came crashing down, and Castiel remembered that he was going home alone tonight to a cold bed and a feisty cat. They slipped out of the booth, and Dean paid the bill and placed a kiss to Beth's cheek before they went out to the car.

“Look Cas, I'll be honest with you. I don't really know what's happening to me right now. I don't know what's going to happen when I get home or come tomorrow morning. I really can't say,” Dean said as he followed Cas' directions to his apartment.

“You don't have to explain it to me, Dean. I understood from the beginning that this wasn't going to change anything,” Castiel admitted softly as he watched the street signs pass by.

“No, Cas. I want you to know that I want nothing more than to take you up to your apartment and let you finish the show, but I can't do that to Lisa. She's seen me through some rough shit, and that's not how I'm going to repay it. But...and I know this is probably pretty shitty, but I'd really like to be friends with you. Judging by tonight, I don't think either of us have enough good friends, and I don't want to lose touch with you again,” Dean finished speaking just as they pulled up to Cas' building.

“I will think about it, Dean. Maybe not right away, but I think I would like to be your friend as well,” Cas said solemnly as he collected his duffel bag, and opened the car door. He bent down before shutting the door, and looked into Dean's eyes on more time. “Even if tonight was traumatic and will probably only lead to pain, I enjoyed our talk very much. I always have,” Cas said then shut the door and let himself into his building. He didn't see the pained expression on Dean's face as he watched Cas walk away.

**Notes for the Chapter:**

> Thank you everyone who has left kudos and comments. I really appreciate all of your support. I really love reading your comments, even if I'm pretty terrible at responding to them. So thanks everyone who keeps reading this!


	6. The Truth Comes Out

Dean pulled into the garage of Lisa's house around 4AM. He was buzzing from the night he spent reacquainting himself with Castiel. He just assumed that everyone had gone to sleep, and he could slip into bed with Lisa. However, when he stepped into the kitchen from the garage, he noticed a dim light coming from the living room. He pulled pulled his over shirt off as he moved toward the light. 

Lisa was sitting in the beige recliner with her legs folded beneath her and a mug of tea resting on her hip. She had the same expression she'd worn the night he'd gone binge drinking after his father's death. It wasn't that she looked upset or disappointed. It was her lack of expression that sent chills down his spine. She looked so devoid of emotion that he wondered if she had fallen asleep with her eyes open.

“Sam called,” she said matter-of-fact, before Dead could say anything. 

Dean looked around the room at the scraps and leftovers from the wedding decorations, and he brought his hand up to rub at the back of his neck.

“What'd he say?” Dean asked tiredly, the buzz of excitement drained.

“He said that you'd run off with the stripper, and that he knew this would happen because you always run off with the strippers,” Lisa said in a voice that still held no distinguishable emotion. 

“Sounds like Sam was pretty drunk.” 

Dean stepped further into the room and moved a binder of wedding plans off the couch, so he could sit. He absently flipped through the protected pages of Lisa's dream wedding plans. 

“Can I explain, or would you rather argue first?” Dean asked calmly as he kept his eyes on the book in his lap instead of on his bride-to-be. 

“Please, explain. I would love to hear this,” Lisa replied, and he could hear the crack in the facade, the hint of feeling that peeked through her practiced apathy. He didn't need to look up to see the wobble of her jaw or the tight creases around her eyes as she held back tears. He looked up anyway, because she deserved to hear this while he looked her in the eye.

“The previous stripper incident was before I met you, so I don't think it's really important right now. Tonight, he wasn't actually a stripper,” Dean started as he sifted through what was pertinent information to relay to Lisa.

“He?” she asked when Dean paused for a moment.

“Yeah, he turned out to be a guy I went to college with, and our mutual... _friend_ ,” he almost choked on how far that one word stretched the truth. “He put Cas up to crashing my bachelor party and stripping for me. Cas ended up having a panic attack, and I made sure he was alright. I was really the only one sober enough to do it. Then we ended up going to a diner and catching up, and we lost track of time,” Dean explained.

Lisa studied him with sad eyes. He noted that he had opened to a page on personalized vows. A note a the top read: _Dean would never go for it, or he'd compare me to pie._ He felt a small pang in his heart as he looked over the samples she'd found, and the love quotes she liked.

“I don't know what to say, Dean. You've been distant for weeks. You've been drinking again. You spend all your free time at the office,” Lisa said as she wiped at the tear that rested on the lid of her right eye. “I thought it was just the promotion, but then I overheard Jess making a comment to Sam about how depressed you look, and it hit me. I didn't want to see it, but you haven't been happy in so long.”

“I'm not depressed—”

“No, Dean. You aren't depressed, you're a caged animal. I love you. I really do, but I think we've both known for a while that we're doing this because it's easy and expected at this point. We've both been going through the motions, because we're both not fully satisfied, but we don't know how to ask for what we need, or we know we can't get what we need from each other. It was comfortable though,” Lisa said calmly, but there was no holding back the tears now. 

Dean was quiet for a moment before he rose from his seat and placed the binder on the coffee table. He leaned over Lisa and lifted her into his strong arms before taking a seat and letting her rest in his lap. He pressed a kiss into her shoulder as she let the tears run down her cheeks.

“I love you too, Lis. And I love Ben,” Dean assured her. He rested his chin on her shoulder and looked again at all of the wedding preparations strewn about. 

“But you're still unhappy. I don't want to be the excuse for you to drink, Dean. I don't want to be a weight on your shoulders, and I don't want to be the wife that makes bitter comments about her husband at fundraisers, because it's the first time in months she's seen him. I don't want people to tell me I should be thankful, because I snagged such a great catch even though we're wrong for each other,” she clung to Dean's hand which tenderly rubbed her arm.

“Dammit, Dean! I was so furious when Sam called, and I waited up just so I could yell at you. Then you came through the door with that smile, the one you used to wear when we started dating. That stupid goofy smile you get when you're thinking about the person you love. It took you nine months to give me that smile, and when I saw it tonight, I just couldn't yell.” 

“I-I'm just so lost right now, Lis. I don't want to hurt you and Ben,” Dean admitted as he too felt a tear slip out. 

“You deserve happiness too, Dean. Sometimes you let imagined responsibilities and others' desires take precedent over your happiness, and I don't know if it's because you are that blindly selfless, or you just don't think you deserve happiness, but please find something or someone that makes you smile like you did tonight all the time. Ben and I have been through knocks before, but we get by,” she said as she twisted to hold his face in her hands, then she kissed his cheek.

“I hope you find that someone too, Lisa. Someone who will write personalized vows for you without sounding like an idiot,” he replied as she pulled away. He was shocked that this was it. He hadn't imagined the night going like this, but then Lisa was always the practical one. All Dean could really do was sit there and listen to all the things he'd tried to shield Lisa from bared before him by none other than the woman herself.

“I will, but that's not your concern anymore,” she said as she slipped her engagement ring into the palm of his hand and climbed out of his lap. “I'll leave your pillow in the spare room,” she said as she walked to the staircase. 

“Sweet dreams, babe,” Dean said as she flicked the hall light off as she went.

“Oh, Dean? You said he was a friend from college. How long have you been in love with him?” Lisa asked softly from the third step. 

“I don't know. I'm not even sure that I do. He's just one of those people that leaves a mark on you. I don't know what it means, but it stays with me,” Dean said as he stared into the empty room, not bothering to face her. Lisa didn't say anything. She nodded though he couldn't see it, then she retreated to their room.

***

Dean was woken from a pleasant dream, which featured an almost naked Cas giving him a lap dance, by his cellphone ringing and what sounded like someone trying to knock down his front door. He rubbed his eyes as he rolled over to answer his phone. He didn't even bother to look at the caller ID as he answered.

“ _Get your ass downstairs and let me in_ ,” Sam yelled over the line. Dean didn't even respond before ending the call. He groaned as he pushed himself out of bed and padded downstairs in just a pair of black boxers and the black t-shirt he'd worn the night before. 

Clearly, Lisa had taken Ben out of the house while he slept, probably to explain it to her family in person. Well, she was definitely a braver person than Dean, because Dean had no desire to open the door and talk to his brother, never mind explain it to all his friends.

Dean pulled the front door open and squinted out into the bright morning light until he was pulled by his t-shirt out the door.

“What the hell did you do, Dean?” Sam shouted as they faced each other on the front porch. Sam was already dressed in his tux, and Dean wondered just how late it was.

“Lisa and I decided that it wasn't going to work out,” Dean said calmly. He ran his fingers through his bedhead lazily while Sam gaped at him.

“What do you mean it wasn't going to work? What happened last night?” Sam demanded, and Dean knew he didn't mean to be accusatory. Sam was just worried for him, the way he was every time Dean fucked up.

“Lisa waited up for me last night, and when I came in, she caught me smiling like a dope. I think we both realized that we weren't making each other happy,” Dean explained vaguely.

“Dean, are you out of your mind? You have everything you could possibly want, and you're throwing it away for some lunatic that crashed your bachelor party to throw himself at you? What happened to the ten year plan? What happened to giving your kids a better life than we had?” Sam shouted at his brother. Dean cringed at the reminder of their rough upbringing.

“I'm not throwing it away for Cas. I'm scrapping the ten year plan for me, because it's slowly eating away at me from the inside out. I spend my days and many of my nights working to represent men far richer than me who think they own the world and can get away with anything. I make that possible for them. And what kind of better life would it be for my kids if their father was still drinking himself to death? So maybe I don't drink because I can't get over mom's death, but I drink because I feel so trapped it's stifling,” Dean said firmly for someone both at a height disadvantage as well as being so obviously under dressed. 

“It's called being an adult, Dean! You have responsibilities, everybody does.”

“Do you want me to be happy, Sam?”

“Of course, I do!”

“Then trust me. Yeah, I've done some stupid shit in the past, including the strippers at your bachelor party. Yeah, I've balked in the face of commitment. Yeah, I had this big ten year plan, but I think I've done a pretty good job of keeping other people out of my messes. I can't drag Lisa and Ben into my own crisis.”

“I just don't understand.”

“You don't _need_ to understand, Sammy. Just trust me,” Dean said with a defeated sigh. He sat on the front steps as he watched Sam pace in his tuxedo. Sam ran a hand over his face as he sat beside his brother. He gripped his knees in frustration as he looked for something to say that wouldn't further hurt Dean.

“When I heard you made partner, I was so damn proud of you. I've looked up to you my whole life, Dean, but then you went at made partner at _31_ and wow. I think I told every single person I came into contact with for a solid two weeks. The guy who makes my coffee in the morning started greeting me with, 'Congrats to your brother, man.' That's how proud I was. You've reached out and grasped all my dreams, and you've shown me that they're attainable. I guess I just can't grasp why you wouldn't want all this,” Sam explained. He gestured at the house and yard. 

Dean looked up from his bare feet with glassy eyes. “Turns out I broke my own heart in college, Sammy. After that, I came up with the ten year plan, which I really thought of as my twenty year plan. The road map that would get me through to middle age when drinking beer and watching the game on the weekends would seem like a special event. Well, I completed the plan at thirty-one. Do you know how bleak my future looks from this seat? I have it all, and now that I'm not fighting for it anymore, I have the time to look at it and realize that I didn't want any of it. I'm an idiot and probably an ungrateful ass, but I'm the only one that has to live with myself.”

Sam looked down at his hands then at Dean's, remembering how there always used to be grease under his fingernails when he was in high school. He remembered how rough Dean's hands were when he'd try to show Sam how to fix the Impala. Dean's hands weren't meant to be as clean and soft as they were now. Dean hadn't learned how to tie until his first law school interview. Dean still insisted on wearing his work boots under his suits when he didn't have to appear in court. Dean had been fighting who he'd chosen to be the whole time, but Sam figured that no one took the time to notice.

“So what is your plan now?” Sam asked.

“I guess I'll start negotiating myself out of my contract. Maybe I'll start my own small practice, or maybe I'll try something else entirely. I'm only thirty-one, I can still become a fireman if I want. I've still got my whole life ahead of me, Sam. I'm going to find something I'll enjoy doing.”

“And someone you enjoy doing it with?” Sam asked with a knowing smirk.

“Yeah, maybe.” Dean said as he shoved his brother in the shoulder fondly. “I really don't want to face everyone,” Dean groaned.

“I think they'll understand, Dean. We give you a hard time, but we just want you to be happy,” Sam said as he pulled his brother into a hug. 

“Alright, that's enough feelings for one day. I think we should call Benny and Ash and get plastered,” Dean said with a smile. Sam rolled his eyes, but he thumbed through his phone for Ash's number. Jess let herself out of their rental car when Sam waved at her, and she immediately rushed over to hug Dean as well. Dean let her squeeze him tightly without complaint. It was actually the most relaxed he'd been in months.

**Notes for the Chapter:**

> Thanks again everyone for the kudos and wonderful comments. Probably only one more chapter and an epilogue left, so we're almost there.


	7. Tearin' Up the Ten Year Plan

Castiel wasn't a drama queen the way that Gabriel was. He didn't turn his pain into a theatrical even to expel it from himself. He brooded in it. It sat inside him and bled into his very being, and packed a little weight onto his already heavy shoulders.

Thus Castiel didn't get roaring drunk when he stumbled into his apartment after Dean dropped him off. He didn't sob or call everyone he knew. He simply went to bed.

Castiel kept to his word after his night with Dean. He refused to answer any of Gabriel's calls, and there were many. The next morning he went to the shelter and looked into adopting another cat. Balthazar was less than thrilled when Castiel brought home another. They didn't get along from the start, and what Castiel had hoped would be a distraction from his troubles just became another headache.

He went to work Monday, and he went through the motions as he always did. Gabriel used every excuse he could find to come check on Castiel, but every time he walked in, he found Castiel carefully editing the next issue. One time Gabriel stopped by, one of the newer contributors was stepping out of Cas' office sobbing. Gabriel raised an eyebrow as he squeezed through the door while she fled.

“Did you just make someone cry? I didn't think you had it in you,” Gabriel commented as he observed the fact that Castiel hadn't shaved in days.

“Her sources were abysmal. Her writing was about as coherent as your average Friday night, and a portion was lifted directly out of an old textbook I just so happened to read in college. We may be a popular science magazine, but we aren't _Cosmo_. My articles need to be based in some sort of fact,” Cas ranted as he tore up the paper copy of her article and threw it up into the air.

Gabriel couldn't hide his worried look, but Castiel wasn't really paying him any attention either. “Cas, I think you might want to take some time off while you...”

“While I what, Gabriel? I'm not sixteen years old. I don't need a carton of ice cream to get over heartache. I am perfectly capable of moving on with my life and forgetting _your_ stupid plan ever happened,” Castiel sounded lethal, and Gabriel was more than a little scared for the next contributing author Castiel called in for a consultation.

“Fine, Cassie, but I'm cutting off your caffeine for the day, and if you make anyone else cry, I'm getting the Powers That Be to send you home,” Gabriel warned as he strode up to Cas' desk, plucked the oversized coffee mug off the cluttered space, and left the room.

Castiel didn't let it bother him. He just reached under his desk to the coffeemaker he'd brought in last week and started drinking out of the pot itself. Gabriel marched right back into the room with a put upon huff, and he yanked the cord of the coffeemaker and left with the whole thing in his hands even as Cas threatened.

Gabriel returned to his own desk and put the coffeemaker right next to the stack of letters that needed sending. He sat down in a defeated slump and tried to think of how to help his best friend because no matter what Cas claimed, the man definitely needed something along the lines of ice cream and romcoms. That's when the thought hit him. He picked up the phone on his desk and dialed a familiar number while he flipped through the stored images on his phone.

“Hey, Luci. I need a number of a client you had last week...of course it's on the party with the stripper crasher...no harm was done. Come on, poor Cas was never going to make the first move...aw don't blame Meg. What was she supposed to do when the owner's brother asked for a favor...hey, don't blame me either. Look, just give me the damn number, so I don't have to resort to more nefarious methods...See you at Sunday dinner,” Gabriel said before he hung up the phone and added a number to his contact list. He sent the picture he'd stored and sat back with a satisfied sigh.

***

Castiel's reign of terror over contributing authors went on for nearly another week. The ordinarily soft spoken man seemed to have finally had enough with the dwindling quality of submitted content, and he was letting everyone know exactly how he felt about it. An email had circulated on Thursday with highlights from emails Cas had sent to several top contributors. Needless to say the office was both in stitches from his stark language and also a bit fearful of coming into contact with him.

Then on Tuesday of the following week, just as lunch hour began, Dean Winchester came strolling into the office wearing a charcoal gray suit with an impeccably tied crimson tie. Connie—one of the administrative assistants—almost fainted when he leaned over her desk asking if Cas was in his office.

“Do you have an appointment, Mr.—”

“Winchester, and no, I'm just stopping by to chat,” he replied with his patented flirty smirk.

“Mr. Winchester. Are you sure you want to speak to Mr. Novak? He's made three grown men cry this week, and it's only Tuesday,” the brunette finished in a conspiratorial whisper.

Dean's smile grew even wider at her words, and he assured her, “I don't scare easily, ma'am.”

The young woman blushed at Dean's suggestive smile, and she pointed to Cas' office at the back of the floor. Dean thanked her and quickly strode across the floor toward Cas' door.

Dean could see someone else in Cas' office with him as he walked through the maze of cubicles. From the looks of it, the man was arguing with Cas and possibly waving around a coffeemaker. Dean frowned as he realized that man was none other than Gabriel.

Dean knocked on the closed door to Cas' office even though he could clearly hear Gabriel yelling about unhealthy caffeine intake and how Cas needed to seriously unclench before he burst a blood vessel from yelling at everyone.

Gabriel only stopped yelling because Castiel froze as soon as he saw Dean standing there.

“Oh great,” Gabriel chirped when he turned to see Dean. Against Cas' demands, Gabriel opened the door and ushered Dean in with a wide grin. “Dean-o, I see you got my messages,” Gabriel said before slipping out the door and closing it firmly. He gave Cas a thumbs up before turning to the entire floor which was watching the proceedings. “Fear not, our salvation has arrived,” he announced to them, loud enough for Dean to hear it through the door.

Cas looked like he might just murder Gabriel where he stood.

“You're probably busy, but I just wanted to stop by and talk for a minute,” Dean said, still standing next to the door.

“Please, take a seat. I'm sure you've been made aware that I'm not the best of company at the moment,” Cas said, motioning to the pair of chairs in front of his desk.

“If I believed everything people said, I wouldn't be a very good lawyer,” Dean told him, taking a seat in the chair closest to the window. “And if I cried easily, I'd have been eaten alive long ago.”

“That's most reassuring because I've run out of tissues,” Cas said, pointing to the empty box sticking out of the trash. Dean laughed at the sight of it, though he felt bad for his part in it, however unexpected it had been. “What brings you to my office, Dean?” Cas asked, sounding tired.

Dean noticed that his tie was loose and not tied very well. He also looked like he'd been running his hands through his hair constantly.

“It's a bit of a story, I guess. The wedding didn't happen. I guess Lisa was a little more observant to the fact we weren't working than I gave her credit for. I've spent the last week negotiating myself out of my contract with the firm, and as of Friday I was free. There are a whole lot of stipulations attached to that freedom, but since I don't have much of a desire to practice law anymore, I'd say I got a clean break. So, I had my car all packed up set to take this long soul-searching roadtrip that I never got to take after college, and I pulled out of my driveway and was cruising down the interstate, and I got this message from a number I didn't recognize,” Dean said, pulling out his phone and sliding it across Cas' desk.

Cas looked down at the screen, and the color drained from his cheeks. “I told him to delete that. He _did_ delete that,” Cas said, staring at the image of him with his shirt torn open, wearing nothing but blue satin panties, a garter belt, and fishnets while holding a glass of wine.

“Yeah, and you trusted Gabriel which was your first mistake. I'm not allowed to practice law in the state right now, so I can't help you sue his ass which I would love to do, so let's just finish my story instead,” Dean told him, tugging the phone back, so Cas might pay attention to him again.

“So, I got this message. I drove 100 more miles, glancing down at it every few minutes. Finally, I pulled into a bar for a late lunch, and I'm sitting in the corner still looking at this picture. It wasn't that you were almost naked or anything that made me keep looking. You looked great and all, but it was just _you_. I spent eight years crushed by your rejection only to learn that you had spent eight years doing the same. Maybe we're both different people now, but I don't think either of us are any happier now than we were back then, and while I was looking at that picture, all I could think was if I keep driving, in eight years, am I still going to be wondering what if? So, I finished my lunch and came back. I don't know if you ever want to speak to me again, but this is it Cas. For the record, so there is no confusion, I've been in love with you since college, and I've done a lot of stupid things to bury it, but it's the truth. I love you, and I may not have a plan anymore, but I want you to be a part of whatever comes next. Is that something you're interested in?” Dean asked, gripping Cas' desk with both hands.

Suddenly, Dean wasn't so sure that he wouldn't cry if Cas rejected him. Dean had never been so nervous about a verdict as he was about Cas' answer. Cas looked so blank as he stared at Dean, then he pushed out of his seat and rifled through his desk drawer for a moment before pulling out a piece of paper that Dean couldn't read and looked Dean right in the eye.

***

“I need a moment, if you'll excuse me,” Castiel said, sounding flat as ever. He saw the way Dean gulped, but he needed to do this. Before Dean could stand, Cas strode out of the room. He marched across the office, ignoring the eyes of his coworkers and their whispers. He marched over to the elevator and once inside pressed the button for the top floor.

He took a steadying breath before the bell dinged, and he stepped out onto the floor. He marched right past Gabriel who was on the phone with God knows who, looking very pleased with himself. Gabe put the phone down as Cas walked past, and he called Cas' name, but Cas ignored it.

He walked right up to Adler's door and pushed inside without even knocking. The man himself was sitting at his desk with one of the administrative assistants from accounting sitting with him, sharing a glass of wine. This was the reason Castiel had to do his job for him. No time to run a magazine when there were employees or investors to take advantage of.

“I resign,” Castiel announced, throwing the letter he'd written the third week he'd worked there and printed every morning with the new date, just in case that was the day he'd work up the nerve.

Adler didn't even have time to question him as the young woman stood and hurried out of the room.

“Effective immediately, I will no longer be providing my services, of which there are many, to this magazine or its affiliates. If you wish to argue breech of contract, I have plenty of evidence at my disposal to counter any of your arguments, including but no limited to misappropriation of company funds for illegal activities including use of prostitutes to secure sponsors. Please don't get up. I can show myself out,” Castiel said as Zachariah tried to stand.

Castiel turned on his heel and marched right back out of the office as Adler began to shout at him. Cas ignored it. He was getting very good at ignoring the things that didn't really matter.

Gabriel wasn't at his desk but standing outside Adler's office with half of the floor. They all looked at him with mouths wide as he walked through their crowd back to the elevators.

Cas got off on his own floor and walked back into his office. Thankfully, Dean was still sitting there looking confused.

“I've never been on a roadtrip,” Cas found himself saying, instead of explaining anything.

“That so? Ever been to the Grand Canyon?” Dean asked, standing up and stepping closer to Cas.

“I have actually. I was eleven and I puked on my burro because I was so terrified we were going to fall over the edge of the trail. He wasn't very happy with me, but we made it to the bottom,” Cas told him.

“Maybe we'll skip the burro ride,” Dean suggested.

“That would be greatly appreciated,” Cas said, laughing at the absurdity of this whole day, this whole week.

“Did you just quit your job for me?” Dean asked, glancing over Cas' shoulder at the bedlam going on out on the floor.

“No, I quit for me. Just like you, this hasn't been working for a long time. I don't know what's next either, but yes Dean it's something I'm interested in. But if you could help me pack up my office before security breaks through Gabe's perimeter of chaos, that would be great,” Cas told him, moving to his desk to start throwing papers and objects into the coffeemaker box under his desk.

Dean laughed, but he quickly jumped to help. “What did you say to your boss that security is coming for you?”

“I may have threatened to tell people certain sensitive information if he gave me any trouble,” Cas said, eyes gleaming with mischief.

“Dude, Gabriel is rubbing off on you. Pass me that trashcan, we can fit stuff in there too,” Dean said, clearing Cas' walls of awards and certificates.

When they emerged with the trash can, the crate he used for recyclables, and his coffeemaker box, everyone was out there including the security personnel, but they were cheering for Cas as he was escorted off the floor.

When they were politely thrown out of the building and told never to return, Cas turned to Dean. He'd never done anything like that before, but it felt good.

“So, what's the plan?” Cas asked, smiling because Dean was practically beaming with joy.

“Fuck the plan, Cas. We're tearin' it up and doing what we want,” Dean proclaimed, grinning as he dropped the crate he was holding and pulled Cas in for a searing kiss. Cas was sure they looked ridiculous, but he didn't much care because this was the freest he'd felt in years, so he dropped his box and wrapped his arms around Dean to savor the kiss.

 

**Notes for the Chapter:**

> We'll it's been well over a year, but there you have it. There will be an epilogue, but this is it for the main story. 
> 
> I'm probably going to go back and do some editing on the whole story before I add the epilogue just to fix some things up since this was one of my first deancas fics, and my writing has evolved a bit since I started it.


	8. Epilogue

**Notes for the Chapter:**

> I can't believe I finished this at this point. I hope you enjoy the conclusion.

Dean was pacing back and forth inside their hotel room. Cas watched him through half lidded eyes. They were both dressed in tuxedos that they'd bought from a thrift store just off the interstate. Cas was pretty sure that none of the pieces went together, but the old woman in charge had given them a discount when they said they'd be getting married in them.

“What the hell is taking him so long?” Dean asked as he continued to pace back and forth in their massive room. Dean had not scrimped when they arrived in Vegas. They'd been doing the whole truck stops and cheap motels thing since they hit the road, but Dean had insisted they do Vegas right. Cas wasn't quite sure what the correct way to do Vegas was, but he couldn't say that he minded the room with the large bar, a hot tub, and a beautiful balcony.

“I'm sure he'll be here soon,” Cas told him calmly. The fact that Sam had dropped everything when Dean called yesterday to tell him they were getting married in Vegas said something about how much Sam loved his brother.

“He showed up for my wedding to Lisa two weeks early. You'd think he could get to our wedding on time,” Dean complained.

“Well, it's easier to get somewhere on time when you weren't told the day before, then expected to drive across the desert to get to the ceremony,” Cas reasoned as he took another sip of beer.

“I'm calling him again,” Dean said, pulling out his phone and dialing Sam's number again. “How much longer?” Dean demanded as soon as someone picked up.

Cas couldn't really tell what was being said on the other end of the line, but Dean began to pace faster. Dean grumbled at the person for another minute before tossing the phone on the bed and climbing on it as well.

“They'll be another hour at least,” Dean told him, crawling over Cas' body.

“That so?”

“I need something to take my mind off of this,” Dean said, giving Cas a significant look as he pressed his hips to Cas'.

“What sort of distraction would this sort of thing require, Dean?” Cas asked, trying to sound grave.

“Something to help me blow off some steam?”

“A shower?”

“No, I'm thinking something more athletic than that...”

“Racquetball?”

“No, I'm thinking something with significantly less clothing required,” Dean said, slowly pulling open Cas' jacket.

“Perhaps yoga? Hot yoga might be possible.”

“I'm thinking the positions I want to put myself in will be more intimate than that.”

“Intimate?”

“Yeah, and penetrating,” Dean was having a hard time keeping a straight face as he unbuttoned Cas' shirt and removed it then unbuttoned his pants as well.

“That does sound distracting,” Cas told him, burying his fingers in Dean's hair as Dean freed his erection from his boxers and took him in his mouth. “Dean, I'm fairly certain that this sort of thing is supposed to happen after the ceremony, not before it,” Cas said, sighing at how good it felt to have Dean suck him down.

“Well, maybe if someone was on time, we'd go about this whole thing the proper way, but...” Dean didn't finish the sentence in favor of swallowing Cas down to the root.

Cas gasped, tugging at Dean's hair as his back arched off the huge bed. There was definitely something to be said about throwing out the script and living life a little.

Since they'd walked out of his office three weeks earlier, they'd seen so much of the country. They'd spent nights under the stars, learning each others bodies. They'd eaten at countless roadside diners. Sometimes one right after another if pie was advertised.

For the first three days, neither of their phones had stopped ringing for more than five minutes at a time. On the morning of the fourth day, Dean had grabbed both of their phones and tossed them in a trashcan outside Bandlands National Park, after they'd stopped along the way to spend a night with Dean's uncle in South Dakota.

It had been mesmerizing to see so much of the country. Dean loved to pull to the side of the road and just watch the landscape while they shared a couple beers, or take Cas hiking. Cas still became breathless thinking about the first time Dean pushed him just off the trail at Yellowstone and got to his knees to give Cas a blowjob while Cas watched the impressive waterfall nearby.

He remembered the full moon rising over the red clay of the desert, having Dean pull over, so they could truly appreciate it. He remembered the way Dean had kissed his neck as the moon illuminated the sky. They'd had sex on the hood of the Impala that night. It was a bit chilly, but it had been perfect. Cas had looked up at the stars as Dean kissed down his chest. Cas didn't think either of them had ever felt so free.

They'd seen the Great Salt Lake, Denver, and Albuquerque. They'd camped beneath the stars whenever they could or in the back of the car. They bathed in rest stop bathrooms sometimes, often getting distracted by each other.

It was like they were in college again instead of men of thirty with successful careers they'd both abandoned. They spent three days exploring the Grand Canyon and the surrounding area. They hiked and discovered. They stopped at roadside stands and bought souvenirs to remember their trip by.

They watched the sun rise and set over the canyon, and even Dean had sat still and seemed to experience the awe of it. They'd talked for hours there, sharing their past successes and failures, their greatest hopes, and their worst fears.

When they drove away, Dean had glanced over at him and grinned.

“That was heavy. I'm thinking we drive down to Tijuana for some fun then we hit Vegas and do it up right,” Dean had suggested, and Cas couldn't have denied him if he'd tried.

Cas thought he might still be recovering from the two nights they'd spent there. They drunk, danced, taken part in what Cas was inclined to call an orgy, though Dean had assured him it had only been casual sex among strangers. Cas thought orgy somehow sounded less sordid. They'd tried surfing, though neither of them were very good. That could have had to do with the hangovers they both had.

Overall, every place they left, they left with great memories and even more hope for the future. Now, they shared a massive suite, and while having sex on every surface was quite fun, Cas couldn't help but think that he didn't need the hot tub or the king sized bed to be happy with Dean. They could live on the road, and Cas would never complain.

Dean swirled his tongue around the head of Cas' cock, bringing Cas back to the present.

“Looks like you're the one that's distracted,” Dean teased, sucking the head with just enough pressure to leave Cas breathless.

“I was thinking about how nice the last few weeks have been,” Cas told him.

“That's great, Cas, but when a guy's sucking your dick, you should probably be thinking about how awesome he is,” Dean laughed, massaging Cas' thighs.

“I'm sorry your ego needs constant tending,” Cas said, gasping when Dean tore his pants off completely and steadied himself over Cas' body. Cas was pretty sure he'd heard his thrift store slacks tear, but there was little to be done when Dean had that look in his eye.

Cas was reduced to gasps and moans as Dean slowly prepared him then sank into him. Cas couldn't think of anything else as Dean slowly made love to him, still half dressed in his own tux.

Not two minutes after they'd both come, there was a knock of the door. Dean pushed himself off of Cas' chest, and looked down at him regretfully.

“Of course, _now_ he arrives,” Dean grumbled as he tugged off the used condom and tossed it in the trash with the others. He tucked himself back into his suit and went to answer the door. However, he dashed back into the room before he did and gave Cas a long searching kiss.

“God Cas, try to look respectable. My brother and his wife are here,” Dean teased, and Cas slapped him upside the head before he ran back out of the room.

\---

Cas wasn't really sure why Dean had chosen the Elvis themed chapel to be married in. Neither of them were particularly big fans of Elvis, and there were any number of themed chapels along the strip. Still, they walked into the chapel at a quarter to ten at night with Sam and Jess at their side.

Cas' pants were duct taped together because Dean had actually ripped them in his haste to get Cas naked. Jess had been kind enough to help him tape them up discretely, without teasing him too much.

When all of the paperwork was done, and they were ready for the ceremony, they walked down the aisle together as Elvis crooned over the speakers. However, Cas stopped halfway up the aisle when he got a good look at the officiant.

“No,” Cas groaned, gripping Dean's forearm tightly.

“Cas, what's wrong?” Dean asked, sounding desperate as he turned to look at Cas. “I thought you wanted to get hitched.”

“I do. I just. How did _he_ know?” Cas asked, pointing to the man dressed as Elvis at the front of the church.

Dean followed his direction and groaned as he realized that the Elvis was none other than Gabriel, in a jumpsuit that was way too tight and a wig. He was swiveling his hips as he sang their procession song, and Cas was a little bit horrified.

“Come on, Cassie! You gotta come up here to get hitched,” Gabe called to them. Cas ran his hand over his face, but he took a breath and grabbed Dean's hand before determinedly marching forward.

“How did you know we were getting married? In Vegas? You aren't an even ordained minister,” Cas hissed. Gabriel was not about to ruin his wedding, no matter how good-intentioned he was or that he was the reason they were marrying in the first place.

“You would not believe how easy it is to get the certification to marry people in Nevada. Also, of course you were going to get married in Vegas. Dean has married in Vegas written all over him,” Gabe told them. “Now, you got your rings? Let's get this show on the road!”

Dean sighed, but he produced the rings they'd bought in their travels. Cas only rolled his eyes a dozen times at Gabriel's customized ceremony. In the end, it didn't matter. He was married to Dean Winchester, the man of his dreams.

“You may now kiss, and I expect tongue,” Gabe told them as they finished their vows.

Dean smiled at him before pulling Cas to him and kissing him slowly while Same, Jess, and Gabe cheered.

 

The End

 

**Author's Note:**

> This probably won't be a terribly long story, maybe 5 or 6 chapters. I'm hoping to update every couple of days, but we'll see what happens. Please, let me know what you think!


End file.
